Triisopropyl borate → 2-Methoxy-5-(trifluoromethyl)phenylboronic acid

HRID 1028637ノート

反応式

HRID 1028637 の反応式
C([Li])CCC.I[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=1[O:17][CH3:18].[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C>C1COCC1>[CH3:18][O:17][C:8]1[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=1[B:19]([OH:24])[OH:20]

参加物

5

反応物 3

HCID 21531Triisopropyl borateHCID 187062962-iodine-4 -(trifluoromethyl) anisoleHCID 178418339Butyllithium

生成物 1

HCID 27826762-Methoxy-5-(trifluoromethyl)phenylboronic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

n-Butyl lithium (1.6M in hexanes, 456 μL, 0.729 mmol) was added dropwise to a stirred solution of 2-iodo-1-methoxy-4-(trifluoromethyl)benzene (Step A, 200 mg, 0.662 mmol) in THF (1.5 mL) at −78° C. under an atmosphere of nitrogen. The reaction stirred at −78° C. for 30 min prior to the addition of triisopropyl borate (458 μL, 1.986 mmol). The reaction stirred an additional 2 h at −78° C. and was quenched with sat. NH4Cl. The mixture was extracted with CH2Cl2 and the organic phase was washed with NaHCO3 (15 mL) and brine (15 mL), dried (Na2SO4), filtered, conc. in vacuo to afford [2-methoxy-5-(trifluoromethyl)phenyl]boronic acid which was carried on without purification.

後処理

  1. stirringThe reaction stirred an additional 2 h at −78° C.
  2. customwas quenched with sat. NH4Cl
  3. extractionThe mixture was extracted with CH2Cl2
  4. washthe organic phase was washed with NaHCO3 (15 mL) and brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered, conc. in vacuo

出典と根拠

ORDレコード
ord-3cd4d6b95d6541fdb506a31e7bbe2ed8
出典データセット
uspto-grants-2014_05
特許番号
US08735435B2

反応ノート

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