Trimethyl borate → 3-Ethoxy-4-fluorobenzeneboronic acid

HRID 1515507ノート

反応式

HRID 1515507 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([O:9][CH2:10][CH3:11])[CH:3]=1.[Li]CCCC.[B:17](OC)([O:20]C)[O:18]C>C1COCC1>[CH2:10]([O:9][C:4]1[CH:3]=[C:2]([B:17]([OH:20])[OH:18])[CH:7]=[CH:6][C:5]=1[F:8])[CH3:11]

参加物

5

反応物 3

HCID 8470Trimethyl borateHCID 598380294-Bromo-2-ethoxy-1-fluorobenzeneHCID 178418339Butyllithium

生成物 1

HCID 445581743-Ethoxy-4-fluorobenzeneboronic acid収率 69%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 9A (3.86 g, 17.6 mmol) in THF (60 mL) at −78° C. was added n-BuLi (1.6 M in hexanes, 14.3 mL, 22.8 mmol). The mixture was stirred at −78° C. for 40 min before trimethyl borate (3.63 mL, 33 mmol) was added. The reaction was left stirring from −78° C. to rt over 4 h. It was quenched with 1.0 N HCl (40 mL), extracted with EtOAc, washed with brine and dried over Na2SO4. After evaporation of the solvent, the crude solid product was triturated with EtOAc/hexanes (1:4). After filtration, 9B (2.2 g, 69% yield) was collected as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.42 (t, J=7.03 Hz, 3H) 4.11 (q, J=7.03 Hz, 2H) 7.03 (dd, J=11.42, 8.35 Hz, 1H) 7.18-7.29 (m, 2H) 7.35 (d, J=7.91 Hz, 1H).

後処理

  1. additionwas added
  2. waitThe reaction was left
  3. customIt was quenched with 1.0 N HCl (40 mL)
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter evaporation of the solvent
  8. customthe crude solid product was triturated with EtOAc/hexanes (1:4)

出典と根拠

ORDレコード
ord-f451a95260c146d8bd02c6da25e347df
出典データセット
uspto-grants-2012_07
特許番号
US08222453B2

反応ノート

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