Potassium Hydroxide → 1-(1-Bromovinyl)-3-chlorobenzene

HRID 357727Notes

Reaction equation

HRID 357727 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([Br:11])[CH2:9]Br)[CH:5]=[CH:6][CH:7]=1.[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[C:8]([Br:11])=[CH2:9]

Participants

4

Procedure

In 50 ml of ethanol was suspended 20.8 g (69.7 mmol) of 3-chloro-α,β-dibromoethylbenzene. To the suspension was added 100 ml of an ethanol solution containing 5.8 g (103.4 mmol) of potassium hydroxide at room temperature, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was poured into 150 ml of ice-water and extracted with 300 ml of diethyl ether. The extract was dried over anhydrous sodium sulfate and concentrated to give 15.0 g (purity: 99%) of 3-chloro-α-bromostyrene. 1H-NMR (CDC13, 8): 5.82 (1H, d), 6.14 (1H, d), 7.26-7.33 (2H, m), 7.45-7.49 (1H, m), 7.57-7.58 (1H, m)

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with 300 ml of diethyl ether
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-99ca9ae8663040e6a01e6cd801436cbc
Source dataset
uspto-grants-1998_11
Patent number
US05841004

Reaction notes

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