Hydrochloric Acid → 3-Bromo-6-(phenylthio)-benzyl alcohol
Reaction equation
[BH4-].[Li+].[Br:3][C:4]1[CH:5]=[C:6]([C:11]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)[C:7](OC)=[O:8].Cl.O>O1CCCC1>[Br:3][C:4]1[CH:5]=[C:6]([C:11]([S:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:12][CH:13]=1)[CH2:7][OH:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A stirred solution of 65 g of lithium borohydride in 1 litre of tetrahydrofuran is treated dropwise under a nitrogen atmosphere over a period of 120 minutes with a solution of 483 g of methyl 3-bromo-6-(phenylthio)-benzoate in 1 litre of tetrahydrofuran. The mixture is stirred for a further 4 hours under reflux. The solution is cooled to 5° C and treated dropwise over a period of 3 hours with 700 ml of 3-N hydrochloric acid. After the addition of approximately 5 litres of water, the mixture is extracted with ether. The organic solution is washed with water and dried over magnesium sulphate. There is obtained crude 3-bromo-6-(phenylthio)-benzyl alcohol as a yellow oil.
Workup
- temperatureunder reflux
- extractionthe mixture is extracted with ether
- washThe organic solution is washed with water
- dry with materialdried over magnesium sulphate
Sources & evidence
- ORD record
- ord-07d7c21559294af7b89fa4437c5ae7b8
- Source dataset
- uspto-grants-1977_02
- Patent number
- US04006144
Reaction notes
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