Tetrahydrofuran → 3-Methyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenylboronic acid

HRID 1666453ノート

反応式

HRID 1666453 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1.C([O:23][B:24](OC(C)C)[O:25]C(C)C)(C)C.C1COCC1.[Li]CCCC>C1(C)C=CC=CC=1>[CH3:19][C:17]1[CH:18]=[C:2]([B:24]([OH:25])[OH:23])[CH:3]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=2)[CH:16]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 21531Triisopropyl borateHCID 668769062-(3-Bromo-5-methylphenoxy)-5-(trifluoromethyl)pyridineHCID 178418339Butyllithium

生成物 1

HCID 668762393-Methyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenylboronic acid収率 121.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-40 °C

実験手順

2-(3-Bromo-5-methylphenoxy)-5-(trifluoromethyl)pyridine (2 g, 0.006 mol) and triisopropylborate (1.66 mL, 0.0072 mol) were dissolved in toluene (40 mL) and THF (20 mL) and cooled to −78° C. n-BuLi (5.38 mL, 0.006 mol) was added while maintaining the reaction at −70° C. The reaction was stirred for 1 h at −40° C. Gradually the temperature was increased to −20-0° C. and the reaction was quenched with 2NHCl. The reaction mixture was warmed to RT, concentrated and extracted with EtOAc. The organic extract was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (2.16 g).

後処理

  1. additionwas added
  2. temperaturewhile maintaining
  3. customthe reaction at −70° C
  4. temperatureGradually the temperature was increased to −20-0° C.
  5. customthe reaction was quenched with 2NHCl
  6. temperatureThe reaction mixture was warmed to RT
  7. concentrationconcentrated
  8. extractionextracted with EtOAc
  9. extractionThe organic extract
  10. dry with materialwas dried over Na2SO4
  11. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-1bdae19e4c0d42208b2cb67c11935435
出典データセット
uspto-grants-2011_10
特許番号
US08044052B2

反応ノート

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