Phosphorus tribromide → 1-(Bromomethyl)-2-methanesulfonylbenzene

HRID 911448Notes

Reaction equation

HRID 911448 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11]O)(=[O:4])=[O:3].P(Br)(Br)[Br:14]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:14][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 22050773(2-Methanesulfonylphenyl)methanol

Product 1

HCID 189224741-(Bromomethyl)-2-methanesulfonylbenzeneYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of (2-methanesulfonyl-phenyl)methanol (735 mg, 3.99 mmol) in dry DCM (2 mL) at 0° C., add a solution of 1M phosphorous tribromide in DCM (6.0 mL, 6.0 mmol) and continue stirring for 1 h. Dilute with saturated aqueous NaHCO3, extract three times with ethyl ether, dry over anhydrous MgSO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (12:1) to provide the title compound as a white solid (950 mg, 97%).

Workup

  1. extractionextract three times with ethyl ether
  2. dry with materialdry over anhydrous MgSO4
  3. concentrationconcentrate in vacuo
  4. customPurify by chromatography on silica gel eluting with hexane/EtOAc (12:1)

Sources & evidence

ORD record
ord-f79206e862aa4842a06435b8aa4432e0
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…