Triisopropyl borate → 4-tert-Butoxyphenylboronic acid

HRID 1600921ノート

反応式

HRID 1600921 の反応式
C([Li])(C)(C)C.[C:6]([O:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7].[B:18](OC(C)C)([O:23]C(C)C)[O:19]C(C)C.[Cl-].[NH4+]>O1CCCC1.CCOCC>[C:6]([O:10][C:11]1[CH:16]=[CH:15][C:14]([B:18]([OH:23])[OH:19])=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7]

参加物

7

反応物 4

HCID 21531Triisopropyl borateHCID 25517Ammonium ChlorideHCID 27639591-Bromo-4-(tert-butoxy)benzeneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 113899354-tert-Butoxyphenylboronic acid

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of tert-butyllithium (1.7 M in pentane, 12 ml, CAUTION-PYROPHORIC) was added dropwise to a stirring solution of 4-bromophenyl tert-butyl ether (2.33 g) in tetrahydrofuran (20 ml) at -70° C. After a further 5 minutes the resulting solution of anion was added dropwise to a solution of triisopropyl borate (6 ml) in tetrahydrofuran (10 ml) at -70 ° C. After the addition was complete the reaction mixture was allowed to warm to room temperature. After 20 minutes a solution of saturated aqueous ammonium chloride (25 ml) and ether (25 ml) was added. The layers were separated and the aqueous phase washed with ether (50 ml). The combined organic extracts were washed with dilute hydrochloric acid (5%, 25 ml) and were then dried over anhydrous magnesium sulfate. The solution was filtered and concentrated under reduced pressure to give a white solid. This was purified by column chromatography over silica eluting with ether then methanol to give the sub-title compound as a white solid (0.69 g).

後処理

  1. additionAfter the addition
  2. customThe layers were separated
  3. washthe aqueous phase washed with ether (50 ml)
  4. washThe combined organic extracts were washed with dilute hydrochloric acid (5%, 25 ml)
  5. dry with materialwere then dried over anhydrous magnesium sulfate
  6. filtrationThe solution was filtered
  7. concentrationconcentrated under reduced pressure
  8. customto give a white solid
  9. customThis was purified by column chromatography over silica eluting with ether

出典と根拠

ORDレコード
ord-9d419f10bead493593b610c80993f2a7
出典データセット
uspto-grants-1999_11
特許番号
US05977105

反応ノート

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