Water → 4-Bromo-2-fluoro-1-(methylsulfonyl)benzene

HRID 2103628Notes

Reaction equation

HRID 2103628 reaction equation
[OH:1]OS([O-])=O.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[C:10]([F:16])[CH:9]=1.[OH2:17]>CO>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:15])(=[O:1])=[O:17])=[C:10]([F:16])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 219340644-Bromo-2-fluorothioanisoleHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 459337204-Bromo-2-fluoro-1-(methylsulfonyl)benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the procedure described for 54d the use of oxone® (1.48 g, 1.57 mmol) in 15 mL water and 4-bromo-2-fluoro-1-methylsulfanyl-benzene (347 mg, 1.57 mmol) in 30 mL methanol after 22 h reaction time gives crude title compound as a white solid. Purify by column chromatography, eluting with a gradient from 100:0 to 20:80 hexanes:ethyl acetate to obtain 4-bromo-2-fluoro-1-methanesulfonyl-benzene (220 mg) as a white solid. 1H-NMR (CDCl3) δ=3.21 (s, 3 H), 7.44-7.53 (m, 2H), 7.84 (mc, 1H).

Workup

  1. customgives crude title compound as a white solid
  2. customPurify by column chromatography
  3. washeluting with a gradient from 100:0 to 20:80 hexanes

Sources & evidence

ORD record
ord-5ba11db8270e403c823ed6009ec12c67
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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