Potassium Carbonate → 3-Bromo-2-methoxy-1,1'-biphenyl

HRID 1042509

반응식

HRID 1042509 반응식
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[C:12]=1[O:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O>[Br:17][C:13]1[C:12]([O:18][CH3:19])=[C:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 181584Benzene, 1,3-dibromo-2-methoxy-

생성물 1

HCID 183474973-Bromo-2-methoxy-1,1'-biphenyl수율 87%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of phenylboronic acid (3.4 g, 28.7 mmol), 2,6-dibromoanisole (22.3 g, 83.8 mmol, 3 equiv.) and palladium tetrakistriphenylphosphine (0.6 g) in ethylene glycol dimethyl ether (50 mL) and a solution of potassium carbonate (10.8 g, 0.078 mol) in water (50 mL) were kept at reflux under nitrogen with good stirring overnight. After cooling, the reaction mixture was partitioned between ethyl acetate (800 mL) and water (400 mL). The organic phase was washed with water (2×400 mL), dried over sodium sulfate and filtered. The solvent was removed in vacuo and the residue was chromatographed on silica (360 g) with heptane (5 L) to afford 6.55 g of pure product (87%).

후처리

  1. temperatureat reflux under nitrogen
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between ethyl acetate (800 mL) and water (400 mL)
  4. washThe organic phase was washed with water (2×400 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customthe residue was chromatographed on silica (360 g) with heptane (5 L)

출처 및 근거

ORD 기록
ord-5a56c11120814a7aaa5d0cc913386c4c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557936B2

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