1-(3-BROMOPHENYL)PYRROLIDINE Chemical Properties

Boiling point:

76/0.1mm

Density 

1.411±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

4.51±0.40(Predicted)

Appearance

Off-white to brown Solid

CAS DataBase Reference

219928-13-9

Safety Information

Hazard Note 

Harmful

HS Code 

2933998090

1-(3-BROMOPHENYL)PYRROLIDINE Usage And Synthesis

Application

1-(3-bromophenyl)pyrrole is a heterocyclic organic compound that can be used to prepare lithium 3-(pyrrolidin-1-yl)benzenesulfinate.

Synthesis

1. To a 500 mL three-necked round-bottomed flask was added a toluene solution (300 mL) of 1,3-dibromobenzene (20 g, 84.78 mmol, 1.00 eq.) under nitrogen protection. 2. To the reaction system was added pyrrolidine (6.03 g, 84.80 mmol, 1.00 eq.), Pd(OAc)2 (190 mg, 0.85 mmol, 0.01 eq.), BINAP (760 mg, 2.53 mmol, 0.03 eq.) and Cs2CO3 (69.1 g, 211.96 mmol, 2.50 equivalent). 3. The reaction mixture was stirred in an oil bath at 120 °C overnight and the progress of the reaction was monitored by TLC (Expander: EtOAc/PE = 1:5). 4. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure by rotary evaporator. 5. The residue was purified by column chromatography (eluent: PE) to afford 8.51 g (45% yield) of 1-(3-bromophenyl)pyrrolidine as a pale yellow liquid. 6. The product was analyzed by LC-MS. 6. The product was characterized by LC-MS: [M+H]+ m/z calculated value C10H13BrN 226, measured value 226.

References

[1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 24, p. 6427 - 6434
[2] Tetrahedron, 2008, vol. 64, # 13, p. 2938 - 2950
[3] Patent: EP3239143, 2017, A2. Location in patent: Paragraph 0165
[4] Patent: US2008/318941, 2008, A1. Location in patent: Page/Page column 44
[5] Patent: US2008/200471, 2008, A1. Location in patent: Page/Page column 66

1-(3-BROMOPHENYL)PYRROLIDINE(219928-13-9)Related Product Information

• 1-(3-BROMOPHENYL)PYRROLIDINE
• 2-(2-Bromophenyl)pyrrolidine
• (R)-2-(2-BROMOPHENYL)PYRROLIDINE
• (S)-2-(2-BROMOPHENYL)PYRROLIDINE
• (S)-2-(4-BROMOPHENYL)PYRROLIDINE
• (3S,4R)-4-(2-BROMOPHENYL)PYRROLIDINE-3-CARBOXYLIC ACID
• (R)-2-(4-BROMOPHENYL)PYRROLIDINE
• N-(4-BROMOPHENYL)PYRROLIDINE,1-(4-BROMOPHENYL)PYRROLIDINE
• (3S,4R)-4-(4-BROMOPHENYL)PYRROLIDINE-3-CARBOXYLIC ACID
• (R)-2-(3-BROMOPHENYL)PYRROLIDINE
• (3S,4R)-4-(3-BROMOPHENYL)PYRROLIDINE-3-CARBOXYLIC ACID
• BOC-(+/-)-TRANS-4-(3-BROMOPHENYL)-PYRROLIDINE-3-CARBOXYLIC ACID
• 1-(3-bromophenyl)pyrrolidin-2-one
• N-(5-Bromo-2-nitrophenyl)-L-proline
• 1-(3-BROMOPHENYL)-5-OXOPYRROLIDINE-3-CARBOXYLIC ACID
• N-(3-BROMOPHENYL)SUCCINIMIDE
• (+/-)-TRANS-4-(3-BROMOPHENYL)PYRROLIDINE-3-CARBOXYLIC ACID HYDROCHLORIDE
• 3-(2-BROMOPHENYL)PYRROLIDINE