Phenacyl bromide → 2-Oxo-2-phenylethyl 4-(bromomethyl)benzoate

HRID 1265495Notes

Reaction equation

C(N(CC)CC)C.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].[Br:18][CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1>C(OCC)(=O)C>[CH2:9]([O:26][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([CH2:19][Br:18])=[CH:21][CH:22]=1)[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11]

Participants

Conditions

Temperature: 50 °C

Procedure

Triethylamine (16 ml, 115 mmol) and bromoacetophenone (22.9 g, 115 mmol) were dissolved in 450 ml of ethyl acetate. The solution was stirred at 50° C. and 4-(bromomethyl)benzoic acid (17.5 g, 155 mmol) was added in seven equal portions over a three hour period. Stirring was continued for an additional 8 hours at 50° C. Precipitated triethylaminehydrobromide was removed by filtration, and the ethyl acetate solution was washed with (3×150 ml each) of 10% citric acid, brine, saturated sodium bicarbonate and brine. The organic phase was dried with sodium sulfate and concentrated in vacuo. The residue was recrystallized from dichloromethane-petroleum ether to give fine white crystals (10.2 g, 27% yield). 1H NMR (DMSO-d6) δ7.99 (m, 4H), 7.69-7.54 (m, 5H), 5.74 (s, 2H), 4.77 (s. 2H); 13C NMR (DMSO-d6) δ193.7, 165.9, 144.6, 134.9, 131.2, 131.0, 130.7, 130.6, 130.2, 129.9, 128.8, 128.6, 68.2, 34.0.

Workup

stirringStirring
customPrecipitated triethylaminehydrobromide was removed by filtration
washthe ethyl acetate solution was washed with (3×150 ml each) of 10% citric acid, brine, saturated sodium bicarbonate and brine
dry with materialThe organic phase was dried with sodium sulfate
concentrationconcentrated in vacuo
customThe residue was recrystallized from dichloromethane-petroleum ether

Sources & evidence

ORD record: ord-9aad9028709246beb217a9679063a5a3
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545162B1

Reaction notes

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