Boron tribromide → HCID 86703344, compound

HRID 2173672Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:13][CH3:14])[C:7]=2[CH:15]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:13][CH3:14])[C:7]=2[CH:15]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 8-methoxy-2,3,4,5-tetrahydro-1-ethylbenzo[b]azepine (0.54 g) in CH2Cl2 (25 mL) cooled to −78° C., BBr3 (1.24 mL) was added, and the reaction allowed to gradually warm to −20° C. After stirring for 3 hours, the reaction was quenched with MeOH, allowed to warm to room temperature, and then concentrated. The residue was dissolved in HCl (1M, 40 mL) and stirred for 1 hour. This solution was brought to pH 12 with K2CO3 (sat. aq.) and extracted with EtOAc (40 mL). The organic layer was washed with brine, dried (Na2SO4) and concentrated. The crude product was purified by silica gel chromatography (gradient of EtOAc in heptane) to provide the title compound (0.37 g) as a clear oil: 1H NMR (DMSO-d6) δ 8.88 (s, 1H), 6.79 (d, 1H); 6.29 (d, 1H), 6.16 (dd, 1H), 3.02 (q, 2H), 2.82-2.79 (m, 2H), 2.57-2.53 (m, 2H), 1.65-1.57 (m, 2H), 1.48-1.42 (m, 2H), 1.09 (t, 3H); MS expected 192 (C12H18NO, M+1), found 192.

Workup

customthe reaction was quenched with MeOH
temperatureto warm to room temperature
concentrationconcentrated
dissolutionThe residue was dissolved in HCl (1M, 40 mL)
stirringstirred for 1 hour
extractionextracted with EtOAc (40 mL)
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe crude product was purified by silica gel chromatography (gradient of EtOAc in heptane)

Sources & evidence

ORD record: ord-b38e1a13690248f584ccb25c12764578
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056885B2

Reaction notes

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