3-Tolylboronic acid → 2-Chloro-5-(3-methyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 2218688Notes

Reaction equation

HRID 2218688 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[CH:12]=[C:13]1[C:19]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=2[CH2:17][CH2:16][C:15]2[CH:25]=[CH:26][CH:27]=[CH:28][C:14]1=2>>[Cl:24][C:22]1[CH:21]=[CH:20][C:19]2[C:13](=[CH:12][C:3]3[CH:4]=[CH:5][CH:6]=[C:1]([CH3:10])[CH:2]=3)[C:14]3[CH:28]=[CH:27][CH:26]=[CH:25][C:15]=3[CH2:16][CH2:17][C:18]=2[CH:23]=1

Participants

3

Reactant 2

HCID 27339503-Tolylboronic acidHCID 688868195-bromomethylene-2-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 689339792-Chloro-5-(3-methyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Procedure

Following procedures essentially as described in Example 219, below, and using m-tolylboronic acid (61 mg, 0.45 mmol) and 5-bromomethylene-2-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (119 mg, 0.37 mmol) provides the title compound. GC/MS data: retention times in minutes (MS data for M+.ion): 19.60 (330), 19.95(330) Mass Spec (EI+) 330.

Sources & evidence

ORD record
ord-5c72aca2887d4a95a70790470b75dae9
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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