Triethylamine → Methanesulfonic acid (R)-3-(4-bromo-3,5-dimethyl-phenoxy)-2-methyl-propyl ester

HRID 237501Notes

Reaction equation

HRID 237501 reaction equation
[Br:1][C:2]1[C:13]([CH3:14])=[CH:12][C:5]([O:6][CH2:7][C@@H:8]([CH3:11])[CH2:9][OH:10])=[CH:4][C:3]=1[CH3:15].[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[C:13]([CH3:14])=[CH:12][C:5]([O:6][CH2:7][C@@H:8]([CH3:11])[CH2:9][O:10][S:17]([CH3:16])(=[O:19])=[O:18])=[CH:4][C:3]=1[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86697161(S)-3-(4-Bromo-3,5-dimethyl-phenoxy)-2-methyl-propan-1-ol

Product 1

HCID 86697162Methanesulfonic acid (R)-3-(4-bromo-3,5-dimethyl-phenoxy)-2-methyl-propyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-3-(4-Bromo-3,5-dimethyl-phenoxy)-2-methyl-propan-1-ol (130 mg), methanesulfonyl chloride (0.073 mL) and triethylamine (0.264 mL) are stirred in 5 mL of dichloromethane at room temperature overnight. The reaction mixture is washed with citric acid saturated aqueous solution and with brine. The organic phase is separated, dried over sodium sulfate and concentrated under vacuum to give the title compound, used in the next step without further purification. Yield: 148 mg.

Workup

  1. washThe reaction mixture is washed with citric acid saturated aqueous solution and with brine
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-aa5dc9ec9e18448b890e0546c1c88e69
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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