Boron tribromide → 4-(4'-Hydroxyphenoxy)biphenyl

HRID 749936ノート

反応式

HRID 749936 の反応式
C[O:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O.ClCCl>ClCCl>[C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:20]=[CH:21][C:3]([OH:2])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 25134Boron tribromideHCID 2668644-(4-Methoxyphenoxy)biphenylHCID 21908982Water methylene chloride

生成物 1

HCID 105634264-(4'-Hydroxyphenoxy)biphenyl収率 50.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

To a solution of the product from step 1 (0.5 g, 1.81 mmol) in dichloromethane (10 mL) at −78° C. was added boron tribromide (1.0 M solution in dichloromethane, 5.43 mL, 5.43 mmol) dropwise over 5-10 min. The subsequent mixture was stirred at −78° C. for an hour followed by ambient temperature for 1 h. After cooling the reaction mixture to 0° C., it was slowly added to cold water/dichloromethane (50 mL/50 mL). The organic portion was washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel flash chromatography using hexane/EtOAc (gradient system) to give the title compound (0.24 g, 47%) as an off-white solid.

後処理

  1. temperatureAfter cooling the reaction mixture to 0° C.
  2. washThe organic portion was washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-217571d23617411da9d8bb5774b30b90
出典データセット
uspto-grants-2008_07
特許番号
US07402684B2

反応ノート

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