2-(5-BroMo-2-Methylbenzyl)-5-(4-fluorophenyl)thiophene Chemical Properties

Melting point:

103 °C

Boiling point:

438.3±40.0 °C(Predicted)

Density 

1.388

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly, Heated), Hexanes (Slightly, Heated)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C18H14BrFS/c1-12-2-5-15(19)10-14(12)11-17-8-9-18(21-17)13-3-6-16(20)7-4-13/h2-10H,11H2,1H3

InChIKey

VLRIERSBZHUCOW-UHFFFAOYSA-N

SMILES

C1(CC2=CC(Br)=CC=C2C)SC(C2=CC=C(F)C=C2)=CC=1

Safety Information

HS Code 

2934999090

2-(5-BroMo-2-Methylbenzyl)-5-(4-fluorophenyl)thiophene Usage And Synthesis

Uses

2-[(5-Bromo-2-methylphenyl)methyl]-5-(4-fluorophenyl)thiophene is an antidiabetic agent that can be used to prepare Canagliflozin (C175190), a sodium-dependent glucose co-transporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes mellitus.

Synthesis

prepares 2-(4-fluorophenyl) thiophene III:
Prepared by Grignard reagent: N 2under protection; magnesium chips (11.7g is added in the 500mL there-necked flask that thermometer, reflux condensing tube, constant pressure funnel be housed; 480mmol), THF (15.0mL), drips 2 p-Fluoro bromo benzenes; add the initiation reaction of 2 iodine post-heating; p-Fluoro bromo benzene (70.0g, 400mmol) is dissolved in THF (250mL), after under reflux, drip the THF solution of p-Fluoro bromo benzene; drip Bi Baowen backflow 2h, GC detection feedstock conversion complete.

Linked reaction: N 2under protection; in the 1000mL there-necked flask that thermometer, reflux condensing tube, constant pressure funnel be housed, add 2-bromothiophene (52.2g, 320mmol), under stirring, add two (methyl ethyl diketone) palladium (23.4mg; 0.0320mmol); THF (200mL), is heated to 50 DEG C, the above-mentioned Grignard reagent prepared of rear dropping; drip to finish and be warming up to 60 DEG C; insulation 1h, GC detect to raw material reaction complete, terminate reaction.System is cooled to 30 DEG C, drips dilute hydrochloric acid (2M, 150mL) under ice-water bath, drips complete vigorous stirring 0.5h, removes ice-water bath and make system naturally rise to room temperature, stratification, water layer CH 2cl 2(100mL × 3) extract, merge organic phase saturated sodium-chloride 200mL to wash, rear drying, concentrating under reduced pressure obtain light tan solid, vacuum-drying to constant weight obtains 2-(4-fluorophenyl) thiophene III (57.4g, 312mmol), it is 98.5% that GC detects purity, and yield is 99.1%.
1H NMR(500MHz,CDCl 3)δ7.65～7.54(m,2H),7.33～7.22(m,2H),7.14～7.03(m,3H).Gc-Ms:178.1.

2-(5-BroMo-2-Methylbenzyl)-5-(4-fluorophenyl)thiophene(1030825-20-7)Related Product Information

• 5-bromo-2-chloro-4’-ethoxydiphenylmethane
• (R)-3-(4-(5-broMo-2-chlorobenzyl)phenoxy)tetrahydrofuran
• 2,3,4,6-Tetrakis-O-trimethylsilyl-D-gluconolactone
• 4-(5-broMo-2-chlorobenzyl)phenol
• 2,3,4,6-TETRA-O-PIVALOYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE
• 5-Bromo-2-methylbenzoic acid
• D-Glucitol, 1,5-anhydro-1-C-[3-[[5-(4-fluorophenyl)-2-thienyl]Methyl]-4-Methylphenyl]-, tetraacetate, (1S)- (9CI)
• (5-broMo-2-Methylphenyl)(5-(4-fluorophenyl)thiophen-2-yl)Methanone
• 2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene
• 5-Bromo-2-methylbenzoyl chloride
• 5-Iodo-2-methylbenzoic acid
• Canagliflozin heMihydrate
• LIPOPHILIC SEPHADEX
• 2-(4-Fluorophenyl)-thiophene
• BCP19353
• Canagliflozin
• 5-Bromo-2-chlorobenzoic acid
• (5-broMo-2-chlorophenyl)(2-ethoxyphenyl)Methanone