Potassium Carbonate → 5-(2-bromo-5-chlorobenzyloxy)-3,4-dihydronaphthalen-1(2H)-one

HRID 1412931Notes

Reaction equation

HRID 1412931 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].[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]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1199215-Hydroxy-1-tetraloneHCID 118465052-Bromo-5-chlorobenzyl bromide

Product 1

HCID 696731795-(2-bromo-5-chlorobenzyloxy)-3,4-dihydronaphthalen-1(2H)-oneYield 94.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-hydroxy-1-tetralone (2.0 g, 12.3 mmol) and 1-bromo-2-(bromomethyl)-4-chlorobenzene (3.6 g, 12.7 mmol) in dimethylformamide (125 mL) was added potassium carbonate (3.5 g, 25.1 mmol). The reaction was stirred under argon for 1 hour 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 (100 mL) and the suspension was agitated for thirty minutes. 5-(2-bromo-5-chlorobenzyloxy)-3,4-dihydronaphthalen-1(2H)-one (4.25 g, 94% 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 (100 mL)
  6. stirringthe suspension was agitated for thirty minutes

Sources & evidence

ORD record
ord-5436ddae5bed40339f474d09f0ae8d40
Source dataset
uspto-grants-2014_12
Patent number
US08921341B2

Reaction notes

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