Thionyl Chloride → 1-(Chloromethyl)-3-methanesulfonylbenzene

HRID 1831919Notes

Reaction equation

HRID 1831919 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH2:11]O)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].S(Cl)([Cl:15])=O>>[Cl:15][CH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 23549738(3-Methanesulfonylphenyl)methanol

Product 1

HCID 220504111-(Chloromethyl)-3-methanesulfonylbenzeneYield 95%

Procedure

A solution of (3-methanesulfonyl)phenyl methanol (0.21 g, 1.1 mmol) in thionyl chloride (3 mL) was heated at 80° C. for 3 h. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure to provide 1-chloromethyl-3-methanesulfonylbenzene as a yellow oil (0.23 g, 95%): 1H NMR (300 MHz, CDCl3) δ 7.98 (s, 1H), 7.90 (d, J=8 Hz, 1H), 7.70 (d, J=8 Hz, 1H), 7.59 (t, J=8 Hz, 1H), 4.65 (s, 2H), 3.08 (s, 3H)

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6b26ad821195475db796931545c69ea2
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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