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Triisopropyl borate → 3-(Neopentyloxysulfonyl)phenylboronic acid

HRID 1989242
ノート
印刷プレビュー

反応式

HRID 1989242 の反応式
[CH3:1][C:2]([CH3:16])([CH3:15])[CH2:3][O:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=1)(=[O:7])=[O:6].[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C.[Li]CCCC>C1COCC1>[CH3:1][C:2]([CH3:16])([CH3:15])[CH2:3][O:4][S:5]([C:8]1[CH:9]=[C:10]([B:17]([OH:22])[OH:18])[CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 21531Triisopropyl borateHCID 574688212,2-Dimethylpropyl 3-bromobenzene-1-sulfonateHCID 178418339Butyllithium2 回

生成物 1

HCID 467389673-(Neopentyloxysulfonyl)phenylboronic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

Step 2) To a solution of the above prepared 3-bromo-benzenesulfonic acid 2,2-dimethyl-propyl ester (9.83 g, 32 mmol) and triisopropyl borate (13.4 mL, 58 mmol) in THF (45 mL) at −78° C. was added n-BuLi (1.6 M in hexane, 20 mL, 32 mmol) keeping the internal temperature below −65° C. Stirring was continued at −78° C. for 1 h, then more n-BuLi (4.0 mL, 6.4 mmol) was added and stirring was continued at −78° C. for 30 min. The reaction mixture was quenched with 1 M H2SO4-sol. (40 mL), allowed to quickly (waterbath) warm to ca. 20° C. and stirred for 10 min. Diluted with EtOAc, layers were separated, washed organic layer with brine and dried over Na2SO4. Removal of the solvent in vacuum left the title compound as white solid (9.00 g, 103%). MS (ISN) 271.4 [(M−H)−].

後処理

  1. customthe internal temperature below −65° C
  2. stirringstirring
  3. waitwas continued at −78° C. for 30 min
  4. customThe reaction mixture was quenched with 1 M H2SO4-sol
  5. stirringstirred for 10 min
  6. additionDiluted with EtOAc, layers
  7. customwere separated
  8. washwashed organic layer with brine
  9. dry with materialdried over Na2SO4
  10. customRemoval of the solvent in vacuum
  11. waitleft the title compound as white solid (9.00 g, 103%)

出典と根拠

ORDレコード
ord-bda6770eb68a400a836d46bdde4624e0
出典データセット
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07642264B2

反応ノート

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