Bromine → 1-Tetralone

HRID 1992946Notes

Reaction equation

HRID 1992946 reaction equation
[F:1][C:2]([F:15])([F:14])[CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:13])[CH2:4]1.[Br:16]Br.C1CCN2C(=NCCC2)CC1>CC#N>[C:5]1(=[O:13])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:12][CH2:3][CH2:4]1.[Br:16][C:4]1[C:3]([C:2]([F:14])([F:15])[F:1])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[OH:13]

Participants

6

Reactant 3

HCID 24408BromineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 137907913-(Trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one

Product 2

HCID 107241-TetraloneHCID 68541215HCID 68541215, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Treatment of 3-(trifluoromethyl)-3,4-dihydro-1(2H)-naphthalenone (178) (0.40 g, 1.87 mmol) with bromine followed by DBU in CH3CN gave 0.23 g (43% from tetralone) of the title compound (179) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 6.45 (s, 1H), 7.58-7.68 (m, 2H), 7.83 (s, 1H), 7.84-7.90 (m, 1H), 8.28 (d, J=7.5 Hz, 1H). LCMS (ESI): m/z 289 (M−H)−.

Sources & evidence

ORD record
ord-52420ee5df454c23820b720c32a3b88e
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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