Hydrochloric Acid → HCID 90291164, compound

HRID 1497506Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[ClH:20]>CN(C)C=O>[Cl:20][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of benzyl (2-bromo-4-hydroxyphenyl)acetate (500 mg) in N,N-dimethylformamide (12.5 mL) was added cuprous chloride (1.62 g), followed by stirring at 140° C. overnight. The reaction mixture was left to be cooled, and then ice water and 1 M hydrochloric acid was added thereto, followed by stirring. After extraction with ethyl acetate, the organic layer was washed with water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain benzyl (2-chloro-4-hydroxyphenyl)acetate (381 mg).

Workup

waitThe reaction mixture was left
temperatureto be cooled
stirringby stirring
extractionAfter extraction with ethyl acetate
washthe organic layer was washed with water
dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThen, the residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-1db39c6314a24a889ceeeae528e95da7
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199927B2

Reaction notes

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