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

HRID 1631505Notes

Reaction equation

HRID 1631505 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-a6a34979c60d41039434a9ebfc9bc964
Source dataset
uspto-grants-2014_07
Patent number
US08791256B2

Reaction notes

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