Diethyl Ether → 1-(4-Amino-3-bromo-phenyl)-ethanone

HRID 1194412Notes

Reaction equation

HRID 1194412 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[Br:11]N1C(=O)CCC1=O.CCOCC.CCCCCC>C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[Br:11]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7468p-AminoacetophenoneHCID 8058HexaneHCID 67184N-bromobutanimide

Product 1

HCID 15152811-(4-Amino-3-bromo-phenyl)-ethanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 48.96 g 4'-aminoacetophenone in 490 ml of toluene was added 64.5 g of solid N-bromosuccinimide in portions over 30 minutes, such that the temperature did not exceed 40° C. Fifteen minutes later, the warm solution was washed with water, dried with sodium sulfate and evaporated in vacuo, giving a dark brown oil, which became crystalline when treated with 20 ml of ether and 80 ml of hexane. The brown crystals were collected, giving 70.5 g of the desired compound, mp 59°-62° C.

Workup

  1. customdid not exceed 40° C
  2. washFifteen minutes later, the warm solution was washed with water
  3. dry with materialdried with sodium sulfate
  4. customevaporated in vacuo
  5. customgiving a dark brown oil, which
  6. customThe brown crystals were collected

Sources & evidence

ORD record
ord-c621fce48909498ba88270a04d512733
Source dataset
uspto-grants-1989_03
Patent number
US04814350

Reaction notes

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