Sodium Hydroxide → 2-Bromo-4,5,6,7-tetrahydro-1-benzothiophen-4-one
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:10])[CH2:7][CH2:8][CH2:9][C:2]1=2.[Br:11]Br.[OH-].[Na+]>C(O)(=O)C.O>[Br:11][C:5]1[S:1][C:2]2[CH2:9][CH2:8][CH2:7][C:6](=[O:10])[C:3]=2[CH:4]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
6,7-Dihydro-4-Benzo[B]thiophenone (1.5 g, 9.86 mmol) was dissolved in acetic acid (10 mL) and water (10 mL). The mixture was cooled to 0° C. and bromine (0.51 mL, 9.86 mmol) was added drop-wise. After 20 min at 0° C. the reaction was warmed to room temperature and stirred for 18 hr. The reaction mixture was cooled in ice and then treated with 1 M aqueous sodium hydroxide solution until the mixture was basic. A precipitate formed which was collected by filtration, washed with water and dried in a vacuum oven at 50° C. to afford the title compound as a grey solid (2.1 g, 96%).
Workup
- temperatureAfter 20 min at 0° C. the reaction was warmed to room temperature
- temperatureThe reaction mixture was cooled in ice
- customA precipitate formed which
- filtrationwas collected by filtration
- washwashed with water
- customdried in a vacuum oven at 50° C.
Sources & evidence
- ORD record
- ord-5baf4a49a1984e8ea1c043f53543fafe
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09233982B2
Reaction notes
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