Phosphorus tribromide → 3-Fluoro-4-(methylsulphonyl)benzyl bromide

HRID 1260665Notes

Reaction equation

HRID 1260665 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:12]O)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].P(Br)(Br)[Br:15]>C(OCC)C.O>[Br:15][CH2:12][C:4]1[CH:5]=[CH:6][C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 672190853-Fluoro-4-(methylsulphonyl)benzyl alcohol

Product 1

HCID 672190653-Fluoro-4-(methylsulphonyl)benzyl bromide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of (3-fluoro-4-methanesulfonyl-phenyl)-methanol (0.269 g, 1.31 mmol) in diethyl ether (5 ml) under an inert atmosphere of Argon is added dropwise phosphorus tribromide (46 μl, 0.434 mmol). After stirring at room temperature overnight, the reaction mixture is diluted with water (2 ml) and the diethyl ether layer separated. This organic portion is placed over NaOH pellets and after 20 minutes, is used as a reagent in solution in diethyl ether.

Workup

  1. customthe diethyl ether layer separated
  2. waitThis organic portion is placed over NaOH pellets and after 20 minutes

Sources & evidence

ORD record
ord-742e340260444d9f9f465ef3beff4e89
Source dataset
uspto-grants-2013_06
Patent number
US08470848B2

Reaction notes

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