3-Nitrophenylboronic Acid → HCID 59770242, compound

HRID 2218733Notes

Reaction equation

HRID 2218733 reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][O:6][C:5]2[C:14]([O:18][CH3:19])=[CH:15][CH:16]=[CH:17][C:4]1=2.[N+:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)([O-:22])=[O:21]>C(OCC)C>[CH3:19][O:18][C:14]1[C:5]2[O:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3/[C:3](=[CH:2]\[C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([N+:20]([O-:22])=[O:21])[CH:28]=3)/[C:4]=2[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 86603985HCID 86603985, compound

Product 1

HCID 59770242HCID 59770242, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following procedures essentially as described in Example 230, 11-bromomethylene-4-methoxy-6,11-dihydro-dibenzo[b,e]oxepine is combined with m-nitrophenyl boronic acid. The pure E isomer is isolated by recrystallization with hexanes and diethyl ether to give 311 mg of product (33% yield). 1H NMR (400 MHz, CDCl3) δ 7.979-7.949 (d, 1H), 7.874 (s, 1H), 7.509-7.491 (d, 1H), 7.365-7.324 (t, 1H), 7.305-7.237 (m, 2H), 7.204-7.162 (t, 1H), 7.123-7.100 (d, 1H), 6.992-6.912 (m, 3H), 6.864-6.840 (d, 1H), 5.75 (broad s, 1H), 5.19 (broad s, 1H), 3.84 (s, 3H).

Sources & evidence

ORD record
ord-36f555c9317242aa8d5d82cd3fedea97
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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