Triethylamine → 4-Bromo-2-chlorobenzyl methanesulfonate

HRID 2181036Notes

Reaction equation

HRID 2181036 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([Cl:10])[CH:3]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][S:19]([CH3:18])(=[O:21])=[O:20])=[C:4]([Cl:10])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 43805739(4-Bromo-2-chlorophenyl)methanol

Product 1

HCID 220586494-Bromo-2-chlorobenzyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-chlorobenzyl alcohol (3.56 g) and anhydrous triethylamine (3 ml) in anhydrous dichloromethane (36 ml) was added dropwise methanesulfonyl chloride (1.4 ml) under a nitrogen flow under ice-cooling. The mixture was stirred for 1 hr and the reaction mixture was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The filtrate was concentrated to give 4-bromo-2-chloro-1-(methanesulfonyloxymethyl)benzene as a pale-brown solid (4.77 g).

Workup

  1. temperaturecooling
  2. washthe reaction mixture was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-27dc2113930a45cb9e7984257b79795b
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

Loading…