N-Bromosuccinamide → HCID 20333849, compound

HRID 1833688Notes

Reaction equation

HRID 1833688 reaction equation
[Br:1][C:2]1[O:3][C:4]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=1.[Br:19]NC(=O)CCC(N)=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[O:3][C:4]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][Br:19])[CH:8]=1

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 20333843HCID 20333843, compound

Product 1

HCID 20333849HCID 20333849, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 22.6 g (0.07 mole) of 2-bromo-5-chloro-3-(3-methylphenyl) benzofuran, 12.5 g (0.07mole) of N-bromosuccinamide in 500 ml of carbon tetrachloride is irradiated and heated with a sun lamp for about 20 hours. The reaction mixture is filtered hot and the filtrate is allowed to cool. A solid forms which is collected, washed with carbon tetrachloride, and dried, then recrystallized from ethyl acetate to provide white product, 2-bromo-3-(3-bromomethylphenyl)-5-chlorobenzofuran, which is used directly in the next step.

Workup

  1. customis irradiated
  2. temperatureheated with a sun lamp for about 20 hours
  3. filtrationThe reaction mixture is filtered hot
  4. temperatureto cool
  5. customA solid forms which is collected
  6. washwashed with carbon tetrachloride
  7. customdried
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f233451edf124f8c8af9c94dc6778336
Source dataset
uspto-grants-1978_01
Patent number
US04066782

Reaction notes

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