Phosphorus tribromide → 1-(Bromomethyl)-2-chloro-4-(methylsulfonyl)benzene

HRID 1254876Notes

Reaction equation

HRID 1254876 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:12]O.P(Br)(Br)[Br:15]>C(OCC)C.O>[Br:15][CH2:12][C:3]1[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 42609245(2-Chloro-4-methanesulfonyl-phenyl)-methanol

Product 1

HCID 27610831-(Bromomethyl)-2-chloro-4-(methylsulfonyl)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.), stirred suspension of (2-chloro-4-methanesulfonyl-phenyl)-methanol (19.1 g, 0.087 mol) in diethyl ether (250 ml) under an inert atmosphere, is treated with phosphorus tribromide (5.2 ml, 0.029 mol) and allowed to stir and warm to room temperature overnight. The resulting mixture is diluted with water (100 ml) and the organic portion is separated and dried over NaOH pellets for 5 minutes. The solvent is removed in vacuo and the resulting crude residue is loaded on a pre-packed Isolute™ silica column and eluted with iso-hexane/ethyl acetate (4:1) to yield the titled compound as a white powder.

Workup

  1. stirringto stir
  2. temperaturewarm to room temperature overnight
  3. customthe organic portion is separated
  4. dry with materialdried over NaOH pellets for 5 minutes
  5. customThe solvent is removed in vacuo
  6. washeluted with iso-hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-1629aa5936684f909b27afcfea3d78af
Source dataset
uspto-grants-2013_06
Patent number
US08455645B2

Reaction notes

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