5-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one → 6-Bromo-1,1-dimethyl-3-p-tolyl-1H-indene

HRID 853197Notes

Reaction equation

HRID 853197 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)=[CH:7][CH2:8][C:9]2(C)[CH3:12])=[CH:4][CH:3]=1.BrC1C=C2C(=CC=1)C(=O)CC2(C)C>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)=[CH:7][C:9]2([CH3:8])[CH3:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 124417825-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one2×HCID 574238127-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydro-naphthalene2×

Product 1

HCID 574238156-Bromo-1,1-dimethyl-3-p-tolyl-1H-indeneYield 75%

Procedure

Following a procedure similar to that for the preparation of 7-bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydro-naphthalene (Compound 4) while using 5-bromo-3,3-dimethyl-indan-1-one (Compound 12, 1.00 g, 4.2 mmol) as the starting material yielded the title compound (981 mg, 75% yield) as a colorless oil:

Sources & evidence

ORD record
ord-cb8cb2c38d0b405993c1e2f03b8a034b
Source dataset
uspto-grants-2007_08
Patent number
US07253319B2

Reaction notes

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