Bromoacetyl bromide → 2-Bromo-2'-acetyl-6'-methylacetanilide

HRID 437894Notes

Reaction equation

HRID 437894 reaction equation
[C:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=1[NH2:6])(=[O:3])[CH3:2].C([O-])(=O)C.[Na+].[Br:17][CH2:18][C:19](Br)=[O:20]>CCOCC>[Br:17][CH2:18][C:19]([NH:6][C:5]1[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:4]=1[C:1](=[O:3])[CH3:2])=[O:20]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 1796281-(2-Amino-3-methylphenyl)ethan-1-oneHCID 517045Sodium Acetate

Product 1

HCID 214273262-Bromo-2'-acetyl-6'-methylacetanilide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 4.8 g of 2-acetyl-6-methylaniline, 3 g of sodium acetate and 120 ml of ether was simultaneously added a solution of 13.2 g of bromoacetyl bromide in 30 ml of ether and 60 g of ice at -3° to 0° C. for 15 minutes. The resultant mixture was stirred at 0° to 5° C. for 2 hours. The ether layer was separated, washed with an aqueous solution of sodium carbonate, dried over anhydrous sodium sulfate and evaporated to give 2-bromo-2'-acetyl-6'-methylacetanilide as crystals. m.p. 97° - 100° C.

Workup

  1. customThe ether layer was separated
  2. washwashed with an aqueous solution of sodium carbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-c4fcef7787f3481989fa2739f961140d
Source dataset
uspto-grants-1977_06
Patent number
US04032573

Reaction notes

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