Bromine → 1-Tetralone

HRID 1992903Notes

Reaction equation

HRID 1992903 reaction equation
COC1C=C(CC(O)C)C=CC=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[CH2:20][CH:19]([CH2:26][CH2:27][C:28]([F:31])([F:30])[F:29])[CH2:18]2.[Br:32]Br.C1CCN2C(=NCCC2)CC1>CC#N>[C:21]1(=[O:25])[C:22]2[C:17](=[CH:16][CH:15]=[CH:24][CH:23]=2)[CH2:18][CH2:19][CH2:20]1.[Br:32][C:20]1[C:19]([CH2:26][CH2:27][C:28]([F:30])([F:29])[F:31])=[CH:18][C:17]2[C:22](=[CH:23][CH:24]=[C:15]([O:14][CH3:13])[CH:16]=2)[C:21]=1[OH:25]

Participants

7

Reactant 4

HCID 24408BromineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 124998521-(3-Methoxyphenyl)propan-2-olHCID 685362636-(Methyloxy)-3-(3,3,3-trifluoropropyl)-3,4-dihydro-1(2H)-naphthalenone

Product 2

HCID 107241-TetraloneHCID 685362622-Bromo-6-(methyloxy)-3-(3,3,3-trifluoropropyl)-1-naphthalenol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Treatment of 6-(methyloxy)-3-(3,3,3-trifluoropropyl)-3,4-dihydro-1(2H-naphthalenone (121) (0.40 g, 1.47 mmol) with bromine followed by DBU in CH3CN gave 0.47 g (92% from tetralone) of the title compound (122) as a white solid. 1H NMR (400 MHz, CDCl3): δ 2.40-2.55 (m, 2H), 3.05-3.10 (m, 2H), 3.91 (s, 3H), 6.06 (s, 1H), 7.02 (d, J=2.5 Hz, 1H), 7.12 (dd, J1=9.1 Hz, J2=2.5 Hz, 1H), 7.20 (s, 1H), 8.10 (d, J=9.1 Hz, 1H). LCMS (ESI): m/z 347 (M−H)−.

Sources & evidence

ORD record
ord-4a729947566148e19eedce03efc65f05
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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