Triethylamine → 1-(Methanesulfonyloxymethyl)-3-bromo-5-(trifluoromethyl)benzene

HRID 355370

Reaction equation

HRID 355370 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[CH2:10][OH:11].C(N(CC)CC)C>ClCCl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:1][S:2]([O:11][CH2:10][C:9]1[CH:12]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:14]=[C:7]([Br:6])[CH:8]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 29919767[3-Bromo-5-(trifluoromethyl)phenyl]methanol

Product 1

HCID 189421641-(Methanesulfonyloxymethyl)-3-bromo-5-(trifluoromethyl)benzeneYield 65.6%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Methanesulfonyl chloride (342 mg) was added dropwise to a stirred solution of 3-bromo-5-(trifluoromethyl)benzyl alcohol (560 mg) and triethylamine (417 μl) in dry dichloromethane (20 ml) at -78° C. under a dry nitrogen atmosphere. The reaction was maintained at -78° C. for 30 minutes and then allowed to warm to room temperature over 2 hours. After this period the reaction mixture was diluted with 5% aqueous citric acid and the organic layers were separated, dried over MgSO4, filtered and the solvent removed under reduced pressure to give 1-(methanesulfonyloxymethyl)-3-bromo-5-(trifluoromethyl)benzene as a yellow oil (480 mg) 1H NMR (360 MHz,CDCl3) δ 3.06 (3H,s),5.24 (2H, s), 7.59 (1H, s), 7.75 (1H, s), 7.94 (1H, s).

Workup

  1. temperatureto warm to room temperature over 2 hours
  2. customthe organic layers were separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a70933ee95ad45b4ab929a9400ac9fed
Source dataset
uspto-grants-1998_11
Patent number
US05830892

Linked notes

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