Dimethyl Carbonate → Methyl(3,5-difluoro-4-methoxybenzoyl)acetate

HRID 1867478Notes

Reaction equation

HRID 1867478 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH3:12])=[C:6]([F:13])[CH:5]=1)=[O:3].[C:14](=O)([O:17]C)[O:15][CH3:16].FSI>>[CH3:16][O:15][C:14](=[O:17])[CH2:1][C:2](=[O:3])[C:4]1[CH:5]=[C:6]([F:13])[C:7]([O:11][CH3:12])=[C:8]([F:10])[CH:9]=1

Participants

4

Reactant 3

HCID 12021Dimethyl CarbonateHCID 27369833',5'-Difluoro-4'-methoxyacetophenoneHCID 18740117HCID 18740117, compound

Product 1

HCID 91003369Methyl(3,5-difluoro-4-methoxybenzoyl)acetateYield 97%

Procedure

This compound was prepared from 3,5-difluoro-4-methoxyacetophenone and dimethyl carbonate according to method A. Yellow solid; Yield: 97%; mp 64-67° C.; 1H-NMR (300 MHz, CDCl3) δ 3.77 (s, 3H), 3.93 (s, 2H), 4.13 (t, J=1.7 Hz, 3H), 7.52 (m, 2H). Minor tautomer: 3.81 (s, 3H), 4.06 (m, 3H), 5.58 (s, 1H), 7.34 (m, 2H), 12.47 (s, 1H); MS (FSI) m/z 243 ([M−H]−), 245 ([M+H]+); Anal. Calcd for C11H10F2O4: C, 54.10; H, 4.13. Found: C, 54.37; H, 4.08.

Sources & evidence

ORD record
ord-70ba92286854466392832f1589fbb2bb
Source dataset
uspto-grants-2009_12
Patent number
US07632845B2

Reaction notes

Loading…