Water → 4-Bromo-1-[(4-fluorobenzene-1-sulfonyl)methyl]-2-nitrobenzene

HRID 1988901Notes

Reaction equation

HRID 1988901 reaction equation
[OH:1]OS([O-])=O.[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[N+:23]([O-:25])=[O:24])=[CH:10][CH:9]=1.[OH2:26]>C(#N)C>[F:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[N+:23]([O-:25])=[O:24])(=[O:1])=[O:26])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 586564724-Bromo-1-{[(4-fluorophenyl)sulfanyl]methyl}-2-nitrobenzene2×

Product 1

HCID 586564814-Bromo-1-[(4-fluorobenzene-1-sulfonyl)methyl]-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of oxone (3.55 g) in water (8 ml) was added to a solution of (4-bromo-2-nitrophenyl)methyl 4-fluorophenyl sulfide (Intermediate 66) (0.52 g) in acetonitrile (10 ml). The mixture was stirred for 5 h filtered and the residue was washed with ethyl acetate. The biphasic filtrate was separated, the aqueous layer was re-extracted with ethyl acetate (2×50 ml) and the combined organic extracts were washed with aqueous sodium metabisulphite (5%, 100 ml) and brine. The dried (MgSO4) extracts were concentrated under vacuum to give the title compound (0.56 g).

Workup

  1. filtrationfiltered
  2. washthe residue was washed with ethyl acetate
  3. customThe biphasic filtrate was separated
  4. extractionthe aqueous layer was re-extracted with ethyl acetate (2×50 ml)
  5. washthe combined organic extracts were washed with aqueous sodium metabisulphite (5%, 100 ml) and brine
  6. dry with materialThe dried (MgSO4) extracts
  7. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-bc569eb1077649669ad044fd26abf42b
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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