Sodium Acetate → 2-Bromo-4-(4-ethoxybenzoyl)benzyl acetate

HRID 1716948Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH2:8]Br.[C:21]([O-:24])(=[O:23])[CH3:22].[Na+]>CN(C=O)C.O>[C:21]([O:24][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:10](=[O:11])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH3:20])=[CH:14][CH:13]=2)=[CH:3][C:2]=1[Br:1])(=[O:23])[CH3:22]

Participants

Conditions

Temperature: 68 °C

Procedure

To a solution of (3-bromo-4-(bromomethyl)phenyl)(4-ethoxyphenyl)methanone (0.456 g, 1.15 mmol) in 15 mL of DMF was added sodium acetate (0.188 g, 2.29 mmol). After being stirred for 2.5 h at 68° C., the mixture was diluted with 15 mL of H2O and extracted 3× with ethyl acetate. The combined organic layers were washed once with saturated NH4Cl, once with saturated brine and dried over Na2SO4. Concentration under reduced pressure gave 0.412 g of the crude product, which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz): δ 7.95 (d, J=1.2 Hz, 1H), 7.79 (d, J=8.8 Hz, 2H), 7.68 (dd, J=1.2, 8.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 1H), 6.95 (d, J=8.8 Hz, 2H), 5.25 (s, 2H), 4.12 (q, J=7.0 Hz, 2H), 1.46 (t, J=7.0 Hz, 3H); MS ESI (m/z) 377 (M+1)+, calc. 376.

Workup

extractionextracted 3× with ethyl acetate
washThe combined organic layers were washed once with saturated NH4Cl, once with saturated brine
dry with materialdried over Na2SO4
concentrationConcentration under reduced pressure

Sources & evidence

ORD record: ord-917a75c88fb848a990c8b8a7c023b8ec
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803778B2

Reaction notes

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