Toluene → HCID 10753742, compound

HRID 747491Notes

Reaction equation

HRID 747491 reaction equation
[C:1]([SH:5])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[Br:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11]Br.C1(C)C=CC=CC=1>CO.O>[Br:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][S:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6387tert-Butyl mercaptanHCID 14798Sodium HydroxideHCID 769652-Bromobenzyl bromide

Product 1

HCID 10753742HCID 10753742, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

36.6 g (406 mmol) of tert-butylmercaptan were added to a mixed solution of 36.5 g (438 mmol) of 48% aqueous sodium hydroxide solution and 400 ml of methanol under a nitrogen atmosphere at room temperature. A solution of 99.5 g (398 mmol) of 2-bromobenzylbromide in 100 ml of methanol were dropped into this solution below 40° C. After stirring for 30 minutes at 40° C. 1000 ml of toluene and 500 ml of water were sequentially added to the reaction solution. The aqueous layer was separated, and the organic layer was sequentially washed with 500 ml of 5% aqueous sodium hydroxide solution and 500 ml of water. After drying the organic layer with magnesium sulfate, the solvent was distilled off to obtain 300 ml of residue, which was used in the next step.

Workup

  1. customThe aqueous layer was separated
  2. washthe organic layer was sequentially washed with 500 ml of 5% aqueous sodium hydroxide solution and 500 ml of water
  3. dry with materialAfter drying the organic layer with magnesium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-1d32d7fa91544bd6a8e845ecbd471adb
Source dataset
uspto-grants-2008_07
Patent number
US07396930B2

Reaction notes

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