Sodium Hydroxide → 2'-acetyl-2-bromo-N-methylacetanilide

HRID 48343Notes

Reaction equation

HRID 48343 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH3:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:16])[CH3:15].[OH-].[Na+]>ClCCl>[C:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N:7]([CH3:6])[C:3](=[O:4])[CH2:2][Br:1])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61147Bromoacetyl bromideHCID 155795831-[2-(Methylamino)phenyl]ethan-1-one

Product 1

HCID 227422572'-acetyl-2-bromo-N-methylacetanilideYield 388.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

404 mg (2 mmol) of bromoacetyl bromide were added to a stirred, ice-cooled solution of 298 mg (2 mmol) of 2′-(methylamino)acetophenone in 5 ml of dichloromethane. The mixture was stirred for 20 minutes then 2 ml of 1M sodium hydroxide solution were added and stirring was continued for a further 15 minutes. The resulting solution was washed with 2M hydrochloric acid and saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated to dryness to give 2.1 g of 2′-acetyl-2-bromo-N-methylacetanilide as a viscous gum. 1H NMR (400 MHz CDCl3) δ: 2.54 (3H,s), 3.16 (3H,s), 3.45-3.52 (2H,q), 7.34 (1H,dd), 7.48 (1H,dt), 7.56 (1H,dt), 7.77 (1H,dd).

Workup

  1. stirringstirring
  2. waitwas continued for a further 15 minutes
  3. washThe resulting solution was washed with 2M hydrochloric acid and saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-7e4046b135ec42f3837a29c43760165d
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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