4-Toluenesulfonyl chloride → 2-(2-Bromophenyl)ethyl 4-methylbenzene-1-sulfonate

HRID 1797292Notes

Reaction equation

HRID 1797292 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH3:21][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:6][CH2:5][CH2:4][C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[Br:1])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 27340892-(2-Bromophenyl)ethan-1-ol

Product 1

HCID 109152412-(2-Bromophenyl)ethyl 4-methylbenzene-1-sulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The reaction and work up was conducted as described in the preparation of compound 163 using 2-bromophenethyl alcohol (5 g, 25 mmol) in pyridine (12 mL) and p-toluenesulfonyl chloride (5.2 g, 27.5 mmol). The crude product was purified by flash chromatography eluting with EtOAc/petroleum ether 1:4. This afforded the title compound as a colourless crystalline compound.

Workup

  1. customThe reaction and work
  2. customThe crude product was purified by flash chromatography
  3. washeluting with EtOAc/petroleum ether 1:4

Sources & evidence

ORD record
ord-2e34e97276ce41f5a1381e8cbd1fb0bc
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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