3-Nitrophenylboronic Acid → HCID 68938368, compound

HRID 2218736Notes

Reaction equation

HRID 2218736 reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([Cl:14])[C:8]=2[CH2:7][O:6][C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]1=2.[N+:19]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)([O-:21])=[O:20]>>[Cl:14][C:13]1[C:8]2[CH2:7][O:6][C:5]3[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=3[C:3](=[CH:2][C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:19]([O-:21])=[O:20])[CH:27]=3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 86603986HCID 86603986, compound

Product 1

HCID 68938368HCID 68938368, compound

Procedure

Following procedures essentially as described in Example 230, 11-bromomethylene-7-chloro-6,11-dihydro-dibenzo[b,e]oxepine is combined with m-nitrophenyl boronic acid to provide the title compound. The pure Z isomer is isolated by crystallization (diethyl ether) to give 1.4 g (31.7% yield) product. 1H NMR (400 MHz, CDCl3) δ 8.038-8.017 (d, 1H), 7.976 (s, 1H), 7.511-7.491 (d, 1H), 7.431-7.410 (d, 1H), 7.369-7.253 (m, 3H), 7.160-7.121 (t, 1H), 7.041-7.005 (m, 2H), 6.928-6.919 (d, 1H), 6.908-6.898 (d, 1H), 5.60 (s, 2H).

Sources & evidence

ORD record
ord-d00fa5bce9184b8b9fa8dd3cfcc84de7
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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