6-Methoxy-alpha-tetralone → 2-bromo-6-methoxy-3,4-dihydronaphthalen-1(2H)-one

HRID 1648340Notes

Reaction equation

HRID 1648340 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][CH2:7][CH2:6]2.[Br:14]Br>CCOCC>[Br:14][CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]1=[O:13]

Participants

4

Reactant 2

HCID 141126-Methoxy-alpha-tetraloneHCID 24408Bromine

Product 1

HCID 116012912-bromo-6-methoxy-3,4-dihydronaphthalen-1(2H)-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6-Methoxytetralone (2.0 g, 11.4 mmol) and bromine (0.6 ml, 11.7 mmol) were refluxed in ether (50 ml) for 30 minutes. The reaction mixture was cooled, concentrated, the residue partitioned between ethyl acetate and dilute NaHSO3. The organic layer was washed with saturated NaHCO3 and water, dried over CaSO4, and concentrated to an oil (2.83 g, 100%); 1H-NMR 8.03 (d, J=9.0Hz, 1H), 6.84 (dd, J1 =9.0 Hz, J2 =2.7 Hz, 1H), 6.69 (d, J=2.3 Hz, 1H), 4.66 (t, J=4.1Hz, 1H), 3.84 (s,3H), 3.20-3.30 (m, 1H), 2.82-2.90 (m, 1H), 2.34-2.50 (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. customthe residue partitioned between ethyl acetate and dilute NaHSO3
  4. washThe organic layer was washed with saturated NaHCO3 and water
  5. dry with materialdried over CaSO4
  6. concentrationconcentrated to an oil (2.83 g, 100%)

Sources & evidence

ORD record
ord-67ae8bdfa19741a6b32d37d1043c6860
Source dataset
uspto-grants-1995_07
Patent number
US05436255

Reaction notes

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