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

HRID 1431790노트

반응식

HRID 1431790 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-339b0d7c21d14382a2b78f668aec5d05
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940718B2

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