Chlorodimethylaluminum → 2-(4-Bromophenyl)-N-methoxy-N-methylacetamide

HRID 735681Notes

Reaction equation

HRID 735681 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].Cl[Al](C)C.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]CC)=O)=[CH:13][CH:12]=1>C(Cl)Cl>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][C:18]([N:3]([O:4][CH3:5])[CH3:2])=[O:20])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 79147ChlorodimethylaluminumHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 7020609Ethyl 2-(4-bromophenyl)acetate

Product 1

HCID 189468992-(4-Bromophenyl)-N-methoxy-N-methylacetamideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask containing N-methyl-N-methoxy amine hydrochloride (878 mg, 9 mmol) in CH2Cl2 (6 mL), a solution of ClAlMe2 (9 mL, 1M, 9 mmol) was added at 0° C. dropwise. The solution was stirred at rt for 30 min. A solution of ethyl 4-bromophenylacetate (1.09 g, 4.05 mmol) was added dropwise at 0° C. The solution was stirred at rt for 1 h, quenched with sat. NH4Cl, and extracted with EtOAc (3×20 mL). The organic layer washed with brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0-50% EtOAc/hexanes) afforded 70A (1.03 g, 80%). MS (ESI) m/z 258.1 (M+H)+.

Workup

  1. stirringThe solution was stirred at rt for 1 h
  2. customquenched with sat. NH4Cl
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe organic layer washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification via flash chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-71fac8bf390041549637903fd737ccc2
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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