Bromine → 1-Tetralone

HRID 1992910Notes

Reaction equation

HRID 1992910 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH2:13][CH2:14][CH3:15])[CH2:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:16][CH3:17].[Br:18]Br.C1CCN2C(=NCCC2)CC1>CC#N>[C:9]1(=[O:12])[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:11]=2)[CH2:6][CH2:7][CH2:8]1.[Br:18][C:8]1[C:7]([CH2:13][CH2:14][CH3:15])=[CH:6][C:5]2[C:10](=[CH:11][C:2]([F:1])=[C:3]([O:16][CH3:17])[CH:4]=2)[C:9]=1[OH:12]

Participants

6

Reactant 3

HCID 24408BromineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68534728HCID 68534728, compound

Product 2

HCID 107241-TetraloneHCID 68537263HCID 68537263, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Treatment of 7-fluoro-6-(methyloxy)-3-propyl-3,4-dihydro-1(2H)-naphthalenone (133) (0.40 g, 1.69 mmol) with bromine followed by DBU in CH3CN gave 0.52 g (98% from tetralone) of the title compound (134) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.01 (t, J=7.3 Hz, 3H), 1.65-1.75 (m, 2H), 2.78 (t, J=7.7 Hz, 2H), 3.98 (s, 3H), 6.05 (s, 1H), 7.07 (d, J=8.2 Hz, 1H), 7.15 (s, 1H), 7.79 (d, J=12.3 Hz, 1H). LCMS (ESI): m/z 313 (M+H)+, m/z 311 (M−H)−.

Sources & evidence

ORD record
ord-4b2750b864454f9a8446e455b1de8794
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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