Dichloromethane → 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

HRID 1413014Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (2.58 g, 6.95 mmol), pyridinium tribromide (2.56 g, 8.0 mmol), dichloromethane (22 mL) and methanol (2.5 mL) was stirred at about 20° C. for 3 hours to obtain a slurry. The precipitated product was filtered, washed with dichloromethane (10 mL) and dried in a vacuum oven at 40° C. to give 9-bromo-3-(2-bromoacetyl)-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one (2.62 g, 84% yield). 400 MHz 1H NMR (CDCl3) δ 8.03-8.01 (m, 1H), 7.85 (d, J=8.2 Hz, 1H), 7.82 (s, 1H), 7.71 (s, 1H), 7.67 (s, 1H), 5.19 (s, 2H), 4.74 (dd, J=4.1, 4.1 Hz, 1H), 4.45 (s, 2H), 3.37-3.29 (m, 1H), 2.99-2.92 (m, 1H), 2.59-2.46 (m, 2H).

Workup

customto obtain a slurry
filtrationThe precipitated product was filtered
washwashed with dichloromethane (10 mL)
customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record: ord-f8f7615db477400b80be8c8fd6217806
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921341B2

Reaction notes

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