Triethylamine → 3-(4-Bromo-3,5-dimethylphenyl)propyl methanesulfonate

HRID 237541Notes

Reaction equation

HRID 237541 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][C:3]=1[CH3:13].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:21][S:22]([O:12][CH2:11][CH2:10][CH2:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Br:1])=[C:3]([CH3:13])[CH:4]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 866971963-(4-Bromo-3,5-dimethylphenyl)propan-1-ol

Product 1

HCID 866972053-(4-Bromo-3,5-dimethylphenyl)propyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 3-(4-bromo-3,5-dimethylphenyl)propan-1-ol (250 mg) and triethylamine (160 μL) in dichloromethane (2 mL) is added methanesulfonyl chloride (850 μL). The mixture is stirred for 12 hours at room temperature. The mixture is partitioned between dichloromethane and saturated aqueous NaHCO3 solution and stirred vigorously for 30 minutes. The organic phase is separated, washed with brine and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→50:50) to give the title compound. Yield: 235 mg; LC (method 8): tR=0.44 min; Mass spectrum (ESI+): m/z=343 [M+Na]+.

Workup

  1. customThe mixture is partitioned between dichloromethane and saturated aqueous NaHCO3 solution
  2. stirringstirred vigorously for 30 minutes
  3. customThe organic phase is separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent is evaporated
  7. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→50:50)

Sources & evidence

ORD record
ord-702c4cbe258d43ec8c1512563516eae2
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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