Trimethyl borate → (2-Fluoro-5-methoxy-4-methylphenyl)boronic acid

HRID 1438167ノート

反応式

HRID 1438167 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7](I)[C:6]([F:10])=[CH:5][C:4]=1[CH3:11].[Li]CCCC.[B:17](OC)([O:20]C)[O:18]C>C1COCC1>[CH3:1][O:2][C:3]1[C:4]([CH3:11])=[CH:5][C:6]([F:10])=[C:7]([B:17]([OH:20])[OH:18])[CH:8]=1

参加物

5

反応物 3

HCID 8470Trimethyl borateHCID 210705041-Fluoro-2-iodo-4-methoxy-5-methylbenzeneHCID 178418339Butyllithium

生成物 1

HCID 57942889(2-Fluoro-5-methoxy-4-methylphenyl)boronic acid収率 69%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 122D (750 mg, 2.8 mmol) in THF (10 mL) was added n-BuLi (1.6M in hexane, 2.3 mL) at −78° C. After stirring for 10 min, trimethyl borate (0.63 mL) was introduced. The mixture was stirred from −78° C. to rt for 3 h before it was quenched by 1N HCl and extracted with ethyl acetate. The organic extracts were washed with saturated Na2S2O3, brine and dried over MgSO4. Evaporation of the solvent gave product 122E (356 mg, 69% yield) as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.18 (s, 3H) 3.80 (s, 3H) 6.80-6.86 (m, 2H).

後処理

  1. stirringThe mixture was stirred from −78° C. to rt for 3 h before it
  2. customwas quenched by 1N HCl
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed with saturated Na2S2O3, brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-b1e4e4c6b4cd4209be662eebae283132
出典データセット
uspto-grants-2009_11
特許番号
US07622585B2

反応ノート

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