Boron tribromide → HCID 14820156, compound

HRID 2372270Notes

Reaction equation

[C:1]([C:9]1[C:21]([O:22]C)=[CH:20][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[N:19])=[C:11]([CH2:24][CH:25]=[CH2:26])[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.[Cl-].[NH4+]>ClCCl>[C:1]([C:9]1[C:21]([OH:22])=[CH:20][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[N:19])=[C:11]([CH2:24][CH:25]=[CH2:26])[CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 0.22 g of 5-(4-benzoyl-5-methoxy-2-allylphenoxy)pentanenitrile, 2.52 ml of a 1M solution of boron tribromide in dichloromethane, and 50 ml of methylene chloride were stirred at -78° C. for two hours. The solution was poured into a cold saturated ammonium chloride solution and ice. The mixture was extracted with ethyl acetate, the organic layer was washed with a cold saturated ammonium chloride solution followed by a saturated sodium chloride solution, dried and concentrated in vacuo. The residue was purified by preparative thin layer chromatography over silica gel eluting with 1:1 ethyl acetate/hexane providing 50 mg of the desired title product, m.p. =60°-62° C. NMR. MS.

Workup

extractionThe mixture was extracted with ethyl acetate
washthe organic layer was washed with a cold saturated ammonium chloride solution
customdried
concentrationconcentrated in vacuo
customThe residue was purified by preparative thin layer chromatography over silica gel eluting with 1:1 ethyl acetate/hexane providing 50 mg of the desired title product
custom=60°-62° C

Sources & evidence

ORD record: ord-4f8ea7c3305f4c50bc7aa924e99cbdea
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05098613

Reaction notes

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