Ethyl bromoacetate → Ethyl (4-acetylphenyl)acetate

HRID 1524854Notes

Reaction equation

HRID 1524854 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:16]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)(=[O:18])[CH3:17].C1COCC1>CCOC(C)=O>[C:16]([C:19]1[CH:24]=[CH:23][C:22]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:21][CH:20]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 37021224-Acetylphenylboronic acid

Product 1

HCID 73716Ethyl (4-acetylphenyl)acetateYield 29.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl bromoacetate (1.70 g, 10.2 mmol), tris-(1-naphthylene)phosphine (379 mg, 0.93 mmol) and tribasic potassium phosphate (10.8 g, 51 mmol) were placed in a flask. The flask was evacuated and back-filled with argon. A solution of 4-acetylphenylboronic acid (2.0 g, 12.2 mmol) in anhyd THF (40 mL) was added to the flask. The reaction was stirred at rt for 16 h. The reaction was diluted with EtOAc, washed with water and brine, dried over MgSO4, filtered and evaporated to dryness. The residue was pre-adsorbed on to SiO2 and the product isolated via SiO2 chromatography to yield 616 mg (29%) of ethyl 4-acetyl-phenylacetate. MS 207.1 (M+H)+.

Workup

  1. customThe flask was evacuated
  2. additionback-filled with argon
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customthe product isolated via SiO2 chromatography

Sources & evidence

ORD record
ord-fe146e087fdd4859aa0f026172af63b2
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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