Boron tribromide → HCID 54527172, compound

HRID 266701Notes

Reaction equation

[C:1]1([NH:7][C:8](=[O:25])[C:9]([C:23]#[N:24])=[CH:10][C:11]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]([O:21]C)=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br>ClCCl>[C:1]1([NH:7][C:8](=[O:25])[C:9]([C:23]#[N:24])=[CH:10][C:11]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14]([OH:21])=[CH:13][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of N-phenyl β-(4-methoxy-5,6,7,8-tetrahydronaphth-1-yl)-α-cyanoacrylamide (3.324 g, 0.01 mol) in anhydrous dichloromethane (100 ml) was added at -78° C. under nitrogen, over a period of 20 min, a 1M boron tribromide solution in dichloromethane (30 ml, 0.030 mol). The resulting mixture was stirred for another 1 h at -78° C. and then allowed to warm up to room temperature. After stirring for 1.5 h at room temperature the mixture was cooled to -10° C. and then quenched by dropwise addition of water (100 ml) over a 10-min period. After addition of ethyl acetate (100 ml) the organic layer was separated, washed with water, dried over Na2SO4 and evaporated under vacuum to dryness. The residue was crystallized from ethanol thus giving pure title compound in 65% yield (2.070 g).

Workup

temperatureto warm up to room temperature
stirringAfter stirring for 1.5 h at room temperature the mixture
temperaturewas cooled to -10° C.
customquenched by dropwise addition of water (100 ml) over a 10-min period
additionAfter addition of ethyl acetate (100 ml) the organic layer
customwas separated
washwashed with water
dry with materialdried over Na2SO4
customevaporated under vacuum to dryness
customThe residue was crystallized from ethanol

Sources & evidence

ORD record: ord-a2db0959c6564e6982ac86fbddcfad2c
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05652250

Reaction notes

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