Triethylamine → HCID 86697220, compound

HRID 237556Notes

Reaction equation

HRID 237556 reaction equation
[Br:1][C:2]1[C:14]([CH3:15])=[CH:13][C:5]([O:6][CH2:7][C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])=[CH:4][C:3]=1[CH3:16].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH3:24][S:25]([O:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][O:6][C:5]1[CH:13]=[C:14]([CH3:15])[C:2]([Br:1])=[C:3]([CH3:16])[CH:4]=1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86697127HCID 86697127, compound

Product 1

HCID 86697220HCID 86697220, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) solution of 3-(4-bromo-3,5-dimethylphenoxy)-2,2-dimethylpropan-1-ol (251 mg) and triethylamine (160 μL) in dichloromethane (3 mL) is added methanesulfonyl chloride (75 μL). The mixture is stirred for 2 days while warming to room temperature. Then the mixture is diluted with dichloromethane, washed with saturated aqueous NaHCO3 solution and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50) to give the title compound. Yield: 271 mg; LC (method 7): tR=1.18 min; Mass spectrum (ESI+): m/z=365 [M+H]+.

Workup

  1. washwashed with saturated aqueous NaHCO3 solution
  2. dry with materialdried (MgSO4)
  3. customThe solvent is evaporated
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50)

Sources & evidence

ORD record
ord-cb7f05d3a8ed419ca4c89a2365e8d331
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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