Boron tribromide → HCID 131719751, compound

HRID 1081570Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]2[CH:21]=[CH:20][C:13]3[CH2:14][C:15]([NH:17][C:18](=[O:19])[C:12]=3[CH2:11]2)=[O:16])=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]2[CH:21]=[CH:20][C:13]3[CH2:14][C:15]([NH:17][C:18](=[O:19])[C:12]=3[CH2:11]2)=[O:16])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 4-(4'-methoxyphenyl)methylenehomophthalimide (279 mg, 1 mmol) in anhydrous dichloromethane (10 ml) is added at -78° C. under nitrogen, over a period of 10 min, a 1.0M solution of boron tribromide in dichloromethane (3 ml, 3 mmol). The resulting mixture is stirred for another 1 h at -78° C. and then allowed to warm to room temperature. After stirring for 1.5 h at 20°-25° C. the mixture is cooled to -10° C. and then quenched by dropwise addition of water (10 ml) over a 10-min period. After addition of ethyl acetate (10 ml) the organic layer is separated, washed with water, dried over Na2SO4 and evaporated under vacuum to dryness. The residue is crystallized from ethanol thus giving pure 4-(4'-hydroxyphenyl)methylenehomophthalimide (186 mg, yield 70%).

Workup

temperatureto warm to room temperature
stirringAfter stirring for 1.5 h at 20°-25° C. the mixture
temperatureis cooled to -10° C.
customquenched by dropwise addition of water (10 ml) over a 10-min period
additionAfter addition of ethyl acetate (10 ml) the organic layer
customis separated
washwashed with water
dry with materialdried over Na2SO4
customevaporated under vacuum to dryness
customThe residue is crystallized from ethanol

Sources & evidence

ORD record: ord-ccf90a10d12b429f8cbee9939770f81a
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05587385

Reaction notes

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