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60469-88-7

3,4-DIBROMOBENZOIC ACID ETHYL ESTER synthesis

2synthesis methods
-

Yield:60469-88-7 84%

Reaction Conditions:

with sulfuric acidReflux;

Steps:

8 Ethyl 3,4-dibromobenzoate (6).

A mixture of 3,4-dibromobenzoic acid (500 mg, 1.79 mmol), cone sulfuric acid (0.2 mL, 2 equiv.) and ethanol (10 mL) was refluxed overnight. After cooling, the mixture was poured onto saturated aq. Na2CCb (5 mL) and concentrated under reduced pressure. The residue was diluted with water (10 mL) and extracted 3 -times withCH2CI2. The combined extracts were dried with Na2SC>4 and concentrated to give a brown oil which solidified on standing. Yield 462 mg (1.65 mmol, 84%). NMR (CDCl3, 400 MHz) d 1.40 (t, J= 7.1 Hz, 3H), 4.38 (q, J= 7.1 Hz, 2H), 7.70 (d, J= 8.3 Hz, 1H), 7.82 (dd, J= 8.3, 2.0 Hz, 1H), 8.27 (d, J= 2.0 Hz, 1H).13C NMR (CDCl3, 100 MHz) d 14.2, 61.6, 125.0, 129.2, 130.2, 131.0, 133.7, 134.6, 164.7. EI-MS mlz 310 (40), 308 (65), 306 (M+, 40), 282 (50), 280 (75), 278 (50), 265 (70), 263 (100), 261 (70), 237 (25), 235 (50), 233 (25), 75 (65), 74 (55). EI- HRMS calcd for M+CiHsBnCh 305.8886, found 305.8893.

References:

WO2020/198742,2020,A1 Location in patent:Page/Page column 56-57