4-Toluenesulfonyl chloride → HCID 131721806, compound

HRID 1107720Notes

Reaction equation

HRID 1107720 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Br:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][OH:21])[CH:16]=[CH:17][CH:18]=1>N1C=CC=CC=1.O>[Br:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][OH:21])[CH:16]=[CH:17][CH:18]=1.[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:10])(=[O:21])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 27340902-(3-Bromophenyl)ethan-1-ol

Product 1

HCID 131721806HCID 131721806, compoundYield 187.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

4-Methylbenzenesulphonyl chloride (4.38 g) was added portionwise to a solution of 3-bromobenzeneethanol [Example H(a)] (2.30 g, 11.4 mmol) in pyridine (30 ml) at 0° C., and the mixture stood at -20° C. for 16 h. The mixture was diluted with water, extracted with diethyl ether, the extracts combined, washed twice with aqueous 4N hydrochloric acid and once with saturated aqueous sodium chloride, dried over sodium sulphate and evaporated to afford a pale yellow oil (3.98 g). [M-OTs]+ 182; 360 MHz 1H n.m.r (CDCl3) 7.66 (2H, d, J 8.3 Hz), 7.34 (1H, dm, J 7.9 Hz), 7.30-7.26 (2H, m), 7.20 (1H, d, J 1.5 Hz), 7.12 (1H, t, J 7.7 Hz), 7.05 (1H, d, J 7.7 Hz), 4.20 (2H, t, J 6.8 Hz), 2.91 (2H, t, J 6.8 Hz), 2.44 (3H, s).

Workup

  1. extractionextracted with diethyl ether
  2. washwashed twice with aqueous 4N hydrochloric acid and once with saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-262c67c4ff6e42928de06c8b03e07f79
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

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