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

HRID 2218663Notes

Reaction equation

HRID 2218663 reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2.[C:18]1([CH3:27])[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=1>>[CH3:27][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2

Participants

3

Reactant 2

HCID 27339503-Tolylboronic acidHCID 52579405-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 597704015-(3-Methyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Procedure

Combine 5-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (0.5 g, 1.75 mmol) and m-tolylboronic acid (0.238 g, 1.75 mmol) using procedures essentially as described in Example 219, below. Pass through a plug of silica gel equilibrated with hexanes. Concentrate the filtrate to give the title product: MS (m/e): 296 (M+); HPLC (ISO80-10M)) t=17.78 min (95%).

Workup

  1. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-98ca3b938c6243b6a503ef81b929a187
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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