Bromine → Ethyl [4-(bromoacetyl)phenyl]acetate

HRID 1524855Notes

Reaction equation

HRID 1524855 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:16]Br>C(Cl)Cl>[Br:16][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 73716Ethyl (4-acetylphenyl)acetate

Product 1

HCID 13027344Ethyl [4-(bromoacetyl)phenyl]acetateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 4-acetyl-phenylacetate from Example 25 Part A (489 mg, 2.4 mmol) was dissolved in CH2Cl2. Bromine (379 mg, 2.4 mmol) was added dropwise. The reaction was stirred at rt for 16 h. The reaction had decolorized from rust red to light yellow. The solvent was evaporated in vacuo to yield 680 mg (99%) of ethyl 2-(4-(2-bromoacetyl)phenyl)acetate as a light yellow oil. The product was used in the next step without further purification. MS 287.0 and 289.0 of equal intensities (M+H)+.

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-851e02e65fe6441f9e82f6a976a9e71b
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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