Water → 2-(4-Fluorophenyl)ethyl 4-methylbenzenesulfonate

HRID 896530Notes

Reaction equation

HRID 896530 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.O>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=2)(=[O:19])=[O:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 820684-Fluorophenethyl Alcohol

Product 1

HCID 173901062-(4-Fluorophenyl)ethyl 4-methylbenzenesulfonateYield 84.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 2-(4-fluorophenyl)ethanol(10.0 g, 71.3 mmol) in pyridine (100 mL) was stirred at −5° C. and treated with 4-toluenesulfonyl chloride (14.95 g, 78.4 mmol). After 3 hours, water (10 mL) was added slowly, followed by dilution with ice water and extraction with chloroform. The organic phase was washed with cold 0.5 M aqueous sulfuric acid, then with water, then with saturated aqueous sodium chloride, and was dried over sodium sulfate. Concentration under vacuum provided a pale orange oil containing residual pyridine. Further concentration under vacuum provided an oil (17.74 g) containing about 10% by weight of residual alcohol. A portion was purified by flash chromatography, eluting with 20% ethyl acetate in hexane, to provide a colorless oil. 1H NMR (300 MHz, CDCl3) δ7.70 (d, J=8 Hz, 2H), 7.30 (d, J=8 Hz, 2H), 7.07 (m, 2H), 6.94 (t, J=9 Hz, 2H), 4.20 (t, J=7 Hz, 2H), 2.94 (t, J=7 Hz, 2H), 2.45 (s, 3H).

Workup

  1. extractionfollowed by dilution with ice water and extraction with chloroform
  2. washThe organic phase was washed with cold 0.5 M aqueous sulfuric acid
  3. dry with materialwith water, then with saturated aqueous sodium chloride, and was dried over sodium sulfate
  4. concentrationConcentration under vacuum
  5. customprovided a pale orange oil
  6. concentrationFurther concentration under vacuum

Sources & evidence

ORD record
ord-99533350f19542d79f4bd70dce96dfba
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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