Boron tribromide → 6-Chloro-2'-fluoro-4-iodobiphenyl-3-ol

HRID 1619695ノート

反応式

HRID 1619695 の反応式
B(Br)(Br)Br.[Cl:5][C:6]1[CH:11]=[C:10]([I:12])[C:9]([O:13]C)=[CH:8][C:7]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21]>ClCCl>[Cl:5][C:6]1[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[CH:8][C:9]([OH:13])=[C:10]([I:12])[CH:11]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 580423152-Chloro-2'-fluoro-4-iodo-5-methoxybiphenyl

生成物 1

HCID 580423466-Chloro-2'-fluoro-4-iodobiphenyl-3-ol収率 94.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Boron tribromide (251 mg, 2.61 mmol) was added to a solution of 2-chloro-2′-fluoro-4-iodo-5-methoxybiphenyl (Preparation 95, 671 mg, 1.85 mmol) in dichloromethane (4.7 mL) at −20° C. and the mixture allowed to warm slowly to room temperature for 18 hours. The reaction was quenched by addition of water (10.0 mL), before being diluted with dichloromethane (30 mL). The organic phase was separated and washed with water (3×5.0 mL), brine (5.0 mL), dried over MgSO4, filtered and evaporated to give a purple oil. Column chromatography purification on silica, eluting with 1:4 ethyl acetate:heptanes gave the title compound (610 mg, 94%) as a colourless oil.

後処理

  1. customThe reaction was quenched by addition of water (10.0 mL)
  2. additionbefore being diluted with dichloromethane (30 mL)
  3. customThe organic phase was separated
  4. washwashed with water (3×5.0 mL), brine (5.0 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give a purple oil
  9. customColumn chromatography purification on silica
  10. washeluting with 1:4 ethyl acetate

出典と根拠

ORDレコード
ord-7566a60786ce43b98753b3a12d84156d
出典データセット
uspto-grants-2014_07
特許番号
US08772293B2

反応ノート

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