Boron tribromide → HCID 22008419, compound

HRID 1493834Notes

Reaction equation

C[O:2][C:3]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:6]2[CH2:7][CH2:8][N:9]([CH3:19])[CH2:10][CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[C:5]=2[CH:4]=1.B(Br)(Br)Br>CO>[OH:2][C:3]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:6]2[CH2:7][CH2:8][N:9]([CH3:19])[CH2:10][CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[C:5]=2[CH:4]=1

Participants

Conditions

Temperature: -70 °C

Procedure

300 mg 7-methoxy-3-methyl-8-nitro-5(2'-methyl-phenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine was dissolved in MeOH and cooled to -70° C. 1 g BBr3 was added slowly and the mixture was stirred for 1 h at -70° C., and stirring was continued for 1 h. Methanol was slowly added to destroy the excess of BBr3 and the mixture was evaporated to dryness. The raw material was purified by column chromatography (kieselgel, CH2Cl2 /CH3OH: 98/2) giving 110 mg of the desired compound. M.p 59°-61° NMR: C5H 5.10d: C6H 6.20S: C9H 8.05s ppm. respectively.

Workup

stirringstirring
waitwas continued for 1 h
customto destroy the excess of BBr3
customthe mixture was evaporated to dryness
customThe raw material was purified by column chromatography (kieselgel, CH2Cl2 /CH3OH: 98/2)

Sources & evidence

ORD record: ord-63b7026382aa4a61811bec7b6fdf165a
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05025009

Reaction notes

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