4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-(4-bromo-phenyl)-2-cyano-2-methyl-ethyl ester

HRID 1022433Notes

Reaction equation

HRID 1022433 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH2:11][OH:12])[C:9]#[N:10])=[CH:4][CH:3]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>N1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:9]#[N:10])([CH3:13])[CH2:11][O:12][S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=2)(=[O:22])=[O:21])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 86704561HCID 86704561, compound

Product 1

HCID 86704562Toluene-4-sulfonic acid 2-(4-bromo-phenyl)-2-cyano-2-methyl-ethyl esterYield 85.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(4-bromo-phenyl)-3-hydroxy-2-methyl-propionitrile (25 g, 104.17 mmol) in pyridine (225 mL) was added para-toluene sulphonyl chloride (29.79 g, 156.25 mmol) and the reaction stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate (300 mL), washed with a 2N aqueous hydrochloric acid solution (2×50 mL), water (2×100 mL), a saturated aqueous sodium bicarbonate solution (2×50 mL), dried over sodium sulfate, and concentrated in vacuo. Flash chromatography (10% ethyl acetate/hexanes) afforded toluene-4-sulfonic acid 2-(4-bromo-phenyl)-2-cyano-2-methyl-ethyl ester as a colorless liquid (35 g, 73%).

Workup

  1. washwashed with a 2N aqueous hydrochloric acid solution (2×50 mL), water (2×100 mL)
  2. dry with materiala saturated aqueous sodium bicarbonate solution (2×50 mL), dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fb53a40c2ce4d2ebb1c2a282dd7221e
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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