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

HRID 1042509

反応式

HRID 1042509 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 183474973-Bromo-2-methoxy-1,1'-biphenyl収率 87%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-5a56c11120814a7aaa5d0cc913386c4c
出典データセット
uspto-grants-2013_10
特許番号
US08557936B2

関連ノート

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