(3-hydroxyphenyl)boronic Acid → HCID 68942661, compound

HRID 2218705Notes

Reaction equation

HRID 2218705 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][CH2:6][C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]1=2.[OH:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1>>[Cl:14][C:13]1[C:8]2[CH2:7][CH2:6][C:5]3[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=3[C:3](=[CH:2][C:22]3[CH:21]=[C:20]([OH:19])[CH:25]=[CH:24][CH:23]=3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 2734359(3-hydroxyphenyl)boronic AcidHCID 688913895-bromomethylene-1-chloro-10,11dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 68942661HCID 68942661, compound

Procedure

Following procedures essentially as described in Example 219, below, and using 5-bromomethylene-1-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (100 mg, 0.313 mmol) and 3-hydroxyphenylboronic acid (47 mg, 0.344 mmol) affords 8 mg (8%) of the Z-isomer of the title compound (MS (ES) 331 (M−H). HPLC shows 95% purity. Continue to elute and isolate 27 mg (26%) of the E-isomer of the title compound, MS (ES) 331 (M−H). HPLC shows 97% purity.

Sources & evidence

ORD record
ord-81c24297720c4e39a904068642536013
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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