Sodium Hydroxide → 10-Bromo-5H-dibenzo[a,d][7]annulen-5-one

HRID 1527830Notes

Reaction equation

[OH-].[Na+].[Br:3][CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=2[CH:5]1Br>CO>[Br:3][C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=2[CH:5]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Sodium hydroxide (51.5 g, 1.29 mmol) was added to a stirring slurry of 10,11-dibromo-10,11-dihydro-dibenzo[a,d]cyclohepten-5-one (2) (157.0 g, 428.9 mmol) in 1.8 L of methanol and the resulting mixture was heated to 70° C. under nitrogen. LC/MS analysis after six hours revealed consumption of the starting material. The slurry was allowed to cool to room temperature and the solid was collected by vacuum filtration, washed with a small amount of methanol, and dried under vacuum to afford 113 g (92%) of 10-bromo-dibenzo[a,d]cyclohepten-5-one (3). ESI MS m/z 286.5, 288.5 (M+H)+. 1H NMR (d6-DMSO, 250 MHz): 8.05 (1H, d), 7.89-7.63 (6H, m), 7.42 (1H, m), 6.67 (1H, s).

Workup

customconsumption of the starting material
temperatureto cool to room temperature
filtrationthe solid was collected by vacuum filtration
washwashed with a small amount of methanol
customdried under vacuum

Sources & evidence

ORD record: ord-b540d21878ac4a6b865f908b0ec6e5b5
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090535B2

Reaction notes

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