Acetyl chloride → Methyl 4-(acetylamino)-2'-bromo-2-biphenylcarboxylate

HRID 269562

Reaction equation

HRID 269562 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]([C:19]([O:21][CH3:22])=[O:20])[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])=[CH:10][CH:11]=1.C(N(CC)CC)C>C(OCC)C.C(OCC)(=O)C>[C:1]([NH:5][C:6]1[CH:7]=[C:8]([C:19]([O:21][CH3:22])=[O:20])[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58730987Methyl 4-amino-2'-bromo-2-biphenylcarboxylate

Product 1

HCID 58731002Methyl 4-(acetylamino)-2'-bromo-2-biphenylcarboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetyl chloride (70 mg, 63 μl, 0.89 mmol) was added to a solution of methyl 4-amino-2′-bromo-2-biphenylcarboxylate (227 mg, 0.74 mmol) and triethylamine (90 mg, 123 ul, 0.89 mmol) in diethyl ether (3 ml) and stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate(10 ml) and washed with 2M HCl, 5% NaHCO3, water and brine the organic phase was dried and evaporated to leave the title compound as a yellow oil (226 mg, 88%).

Workup

  1. washwashed with 2M HCl, 5% NaHCO3, water and brine the organic phase
  2. customwas dried
  3. customevaporated

Sources & evidence

ORD record
ord-028f0a6b94334a54b8bbeb8546e3a98f
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Linked notes

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