Bromine → HCID 68537594, compound

HRID 1992881Notes

Reaction equation

HRID 1992881 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH:7]([CH2:14][CH2:15][CH3:16])[CH2:6]2.[Br:17]Br.C1CCN2C(=NCCC2)CC1>CC#N>[Br:17][C:8]1[C:7]([CH2:14][CH2:15][CH3:16])=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]=1[OH:13]

Participants

5

Reactant 3

HCID 24408BromineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68537219HCID 68537219, compound

Product 1

HCID 68537594HCID 68537594, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Treatment of 6-(methyloxy)-3-propyl-3,4-dihydro-1(2H)-naphthalenone (93) (0.50 g, 2.29 mmol) with bromine followed by DBU in CH3CN gave 0.62 g of compound 94 as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 1.01 (t, J=7.4 Hz, 3H), 1.65-1.75 (m, 2H), 2.79 (t, J=7.7 Hz, 2H), 3.90 (s, 3H), 6.06 (s, 1H), 7.00 (d, J=2.4 Hz, 1H), 7.08 (dd, J1=9.1 Hz, J2=2.4 Hz, 1H), 7.17 (s, 1H), 8.07 (d, J=9.1 Hz, 1H). LCMS (ESI): m/z 295 (M+H)+, m/z 293 (M−H)−.

Sources & evidence

ORD record
ord-1ed7d7950e9c4c34b4cb04615ed34e95
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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