Potassium Carbonate → 7-((2-Bromo-5-chlorophenyl)methoxy)-1,2,3,4-tetrahydronaphthalen-1-one

HRID 590646Notes

Reaction equation

HRID 590646 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[CH2:21]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[CH2:21][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5718187-hydroxy-3,4-dihydro-2H-naphthalen-1-oneHCID 118465052-Bromo-5-chlorobenzyl bromide

Product 1

HCID 696728137-((2-Bromo-5-chlorophenyl)methoxy)-1,2,3,4-tetrahydronaphthalen-1-oneYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 7-hydroxy-1-tetralone (13.9 g, 85.7 mmol) and 1-bromo-2-(bromomethyl)-4-chlorobenzene (25.6 g, 90.0 mmol) in dimethylformamide (850 mL) was added potassium carbonate (24 g, 172 mmol). The reaction was stirred under argon for 18 hours then diluted with ethyl acetate (1 L). The organics were washed three times with water and once with brine. The organic layer was then dried with magnesium sulfate, filtered and concentrated. To the resulting oil was added methanol (500 mL) and the suspension was agitated for thirty minutes. 7-(2-bromo-5-chlorobenzyloxy)-3,4-dihydronaphthalen-1(2H)-one (27.8 g, 89% yield) was isolated by filtration.

Workup

  1. washThe organics were washed three times with water
  2. dry with materialThe organic layer was then dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionTo the resulting oil was added methanol (500 mL)
  6. stirringthe suspension was agitated for thirty minutes

Sources & evidence

ORD record
ord-57804090d2864e70bd29990be4f86aa4
Source dataset
uspto-grants-2016_01
Patent number
US09233974B2

Reaction notes

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