Triethylamine → Ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoate

HRID 389697Notes

Reaction equation

[C:1]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[BrH:24].[NH+]1C=CC=CC=1.CCOC(C)=O>C(O)C>[Br:24][CH:11]([C:1]([C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)=[O:10])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl p-anisoylacetate (1.00 g, 4.5 mmol) in ethanol (14 mL) at 50° C. was added triethylamine (0.63 mL, 4.5 mmol) followed by pyridinium hydrobromide perbromide (1.44 g, 4.5 mmol) and the resulting mixture was then stirred at 50° C. for 2 hours. The reaction was cooled to room temperature and poured into EtOAc. The organic phase was then washed with saturated sodium bicarbonate solution and 0.5M aqueous HCl, dried over MgSO4 and the solvent removed in vacuo to afford ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoate (1.209 g, 4.0 mmol, 89%) which was used without further purification. 1H NMR (CDCl3) δ 1.26 (3H, t), 3.89 (3H, s), 4.28 (2H, q), 5.62 (1H, s), 6.96 (2H, d), 7.98 (2H, d). LCMS (2) Rt: 3.06 min; m/z (ES+) 301/303.

Workup

temperatureThe reaction was cooled to room temperature
washThe organic phase was then washed with saturated sodium bicarbonate solution and 0.5M aqueous HCl
dry with materialdried over MgSO4
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-1affa2de650e424bbda8d18fd575800b
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378095B2

Reaction notes

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