Benzenesulfonyl chloride, 5-fluoro-2-methoxy- (9CI) Chemical Properties

Boiling point:

309.8±27.0 °C(Predicted)

Density 

1.455±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

crystals

color 

Off white

InChI

InChI=1S/C7H6ClFO3S/c1-12-6-3-2-5(9)4-7(6)13(8,10)11/h2-4H,1H3

InChIKey

LUEBMKPHZDSPFH-UHFFFAOYSA-N

SMILES

C1(S(Cl)(=O)=O)=CC(F)=CC=C1OC

Safety Information

RIDADR 

UN3261

HazardClass 

IRRITANT

HS Code 

2909309090

Benzenesulfonyl chloride, 5-fluoro-2-methoxy- (9CI) Usage And Synthesis

Uses

5-Fluoro-2-methoxybenzenesulfonyl chloride

Synthesis

The general procedure for the synthesis of 5-fluoro-2-methoxybenzenesulfonyl chloride from 4-fluoroanisole was as follows: 1-fluoro-4-methoxybenzene (10.0 g, 0.079 mol) was slowly added dropwise to sulfuryl chloride (31.4 ml, 0.474 mol) at 0 °C. The reaction mixture was stirred at room temperature for 6 h, followed by slow dropwise addition to ice water for quenching. The mixture was extracted three times with dichloromethane (CH2Cl2). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the target product 5-fluoro-2-methoxybenzenesulfonyl chloride (15.0 g, 84.6% yield). The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 3.74 (s, 3H), 6.97 (dd, J = 4.3, 8.9 Hz, 1H), 7.13 (dt, J = 3.4, 8.6 Hz, 1H), 7.41 (dd, J = 3.3, 8.8 Hz, 1H).

References

[1] Patent: WO2010/31, 2010, A1. Location in patent: Page/Page column 86
[2] Tetrahedron, 2016, vol. 72, # 47, p. 7570 - 7578
[3] Patent: WO2013/126608, 2013, A1. Location in patent: Paragraph 00812
[4] Patent: WO2005/18529, 2005, A2. Location in patent: Page/Page column 54
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 8, p. 1735 - 1746