4-Toluenesulfonyl chloride → (4-Bromophenyl)methyl 4-methylbenzene-1-sulfonate

HRID 1976206Notes

Reaction equation

HRID 1976206 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=1)([O:9][CH2:8][C:7]1[CH:10]=[CH:11][C:4]([Br:3])=[CH:5][CH:6]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 11371239(4-Bromophenyl)methyl 4-methylbenzene-1-sulfonateYield 22.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium hydride (257 mg, (428 mg of 60% dispersion), 10.6 mmol, 2 eq) was added to a solution of p-bromobenzyl alcohol (1 g, 5.3 mmol) in dry toluene (30 mL). Once the concomitant effervescing had ceased, p-toluenesulphonyl chloride (2.04 g, 10.6 mmol, 2 eq) was added and the mixture stirred at room temperature, 12 hours. The toluene was removed in vacuo and the residue taken up in water and extracted into ethyl acetate portions. The combined organic layers were washed (brine), dried (MgSO4), filtered, and concentrated in vacuo to give the crude product which was purified by column chromatography (silica gel, eluant:ethyl acetate/heptane mixtures) to give the p-bromobenzyl tosylate as a white solid (yield: 400 mg, 22%);

Workup

  1. customThe toluene was removed in vacuo
  2. extractionextracted into ethyl acetate portions
  3. washThe combined organic layers were washed (brine)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product which
  8. customwas purified by column chromatography (silica gel, eluant:ethyl acetate/heptane mixtures)

Sources & evidence

ORD record
ord-b737b8ecc6fb4545ba02b564cbb2d395
Source dataset
uspto-grants-2001_05
Patent number
US06225352B1

Reaction notes

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