Bromine → HCID 90422969, compound

HRID 531023Notes

Reaction equation

C(=O)(O)[O-].[Na+].[CH2:6]([O:13][C:14]1[CH:23]=[C:22]([CH:24]2[CH2:27][CH2:26][CH2:25]2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:28]Br>ClCCl>[CH2:6]([O:13][C:14]1[CH:23]=[C:22]([CH:24]2[CH2:27][CH2:26][CH2:25]2)[C:21]([Br:28])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 10 °C

Procedure

Sodium bicarbonate (7.51 g) was added to a mixture of methyl 2-(benzyloxy)-4-cyclobutylbenzoate (14 g) and dichloromethane, then a dichloromethane (25 mL) solution of bromine (3.17 mL) was slowly added thereto at 10° C., and the mixture was stirred at the same temperature as above for 1 hour. A saturated aqueous solution of sodium bicarbonate was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bisulfite and saturated saline and then dried over anhydrous sodium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (12.2 g).

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with a saturated aqueous solution of sodium bisulfite and saturated saline
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-954ef1045ab74fa0b3115530a210d936
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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