p-Toluenesulfonic acid monohydrate → 5-Bromo-1-benzothiophene
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH2:8][CH:7](O)[C:6]=2[CH:11]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To acetone (600 mL) solution of 300 g of 5-bromo-2,3-dihydro-1-benzothiophen-3-ol was added 12.4 g of p-toluenesulfonic acid monohydrate, which was then refluxed for 2 hours. To the reaction solution was added 15.0 g of activated carbon, which was then stirred. Insoluble matter was filtered off and washed with 300 mL of acetone. The filtrate and washings were combined, to which was dropwise added 2700 mL of water at 5 to 15° C. The precipitate was collected by filtration to provide 268 g of 5-bromo-1-benzothiophene as pale purple solid form.
Workup
- temperaturewas then refluxed for 2 hours
- additionTo the reaction solution was added 15.0 g of activated carbon, which
- filtrationInsoluble matter was filtered off
- washwashed with 300 mL of acetone
- customat 5 to 15° C
- filtrationThe precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-46703aa5d66b443b9087d1fcd3ddd03a
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951963B2
Reaction notes
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