Water → 5-Bromo-2-chloro-4-(methoxycarbonyl)benzoic acid
Reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([Cl:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1OCCOCCOCCOCCOCC[O:16]C1.C(O)(C)(C)C.[OH2:37]>>[Br:1][C:2]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][C:9]([Cl:13])=[C:10]([CH:11]=1)[C:12]([OH:16])=[O:37]Participants
Conditions
- Temperature
- 55 °C
Procedure
A mixture of methyl 2-bromo-5-chloro-4-methylbenzoate (39.53 g, 0.15 mol), 18-Crown-6 (3.95 g), tert-butyl alcohol (350 mL), and water (750 mL) was combined together with mechanical stirring. The reaction mixture was heated to reflux and monitored by TLC. After refluxing overnight, the reaction was cooled to 55° C. and filtered. The filter cake was washed with hot water (2×100 mL, 50° C.). The filtrate was neutralized with 18% hydrochloric acid to pH 1 and stored in a refrigerator (0˜5° C.) for 3 h. It was filtered, and then washed with ice water (2×50 mL) and petroleum ether (2×50 mL). The filter cake was dried under vacuum to give the title compound as a white crystalline solid. Yield: 32.1 g (73%). 1H-NMR (DMSO-d6, 300 MHz): δ 8.10 (s, 1H), 7.89 (s, 1H), 3.86 (s, 3H).
Workup
- temperatureThe reaction mixture was heated
- temperatureto reflux
- temperatureAfter refluxing overnight
- filtrationfiltered
- washThe filter cake was washed with hot water (2×100 mL, 50° C.)
- filtrationIt was filtered
- washwashed with ice water (2×50 mL) and petroleum ether (2×50 mL)
- customThe filter cake was dried under vacuum
Sources & evidence
- ORD record
- ord-d49890a43f9e4c6c8fa0c0d75617ca8d
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07838498B2
Reaction notes
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