10,11-dihydro-5H-dibenzo(a,d)cycloheptene → HCID 59770478, compound

HRID 2218624Notes

Reaction equation

HRID 2218624 reaction equation
[CH2:1]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.[Br:16][C:17]1[CH:24]=[C:21]([CH:22]=O)[C:20]([O:25][CH3:26])=[CH:19][CH:18]=1>>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([O:25][CH3:26])=[C:21]([CH:24]=1)[CH:22]=[C:9]1[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:2][CH2:1][C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2

Participants

3

Reactant 2

HCID 7002910,11-dihydro-5H-dibenzo(a,d)cyclohepteneHCID 906845-Bromo-2-methoxybenzaldehyde

Product 1

HCID 59770478HCID 59770478, compoundYield 65.5%

Procedure

Following the procedures essentially as described for Preparation 5 and Example 28 above, using dibenzosuberane (15.0 g, 77.2 mmol) and 5-bromo-o-anisaldehyde (16.6 g, 77.2 mmol), recrystallization from boiling toluene/hexanes affords 19.78 g (65%) of the title compound as a tan solid. 1H-NMR (CDCl3) δ 2.76-3.70 (br m, 4H), 3.81 (s, 3H), 6.69 (d, 1H), 6.76 (d, 1H), 6.88-7.29 (m, 9H), 7.53 (m, 1H); HPLC shows 100% purity.

Workup

  1. customas described for Preparation 5 and Example 28 above,

Sources & evidence

ORD record
ord-14b35a41bf464dea9adfb761c749a31d
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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