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Triisopropyl borate → 3-(Neopentyloxysulfonyl)phenylboronic acid

HRID 1927965
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HRID 1927965 반응식
[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]
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참가 물질

5

반응물 3

HCID 21531Triisopropyl borateHCID 574688212,2-Dimethylpropyl 3-bromobenzene-1-sulfonateHCID 178418339Butyllithium2회

생성물 1

HCID 467389673-(Neopentyloxysulfonyl)phenylboronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
20 °C

실험 절차

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)−].

후처리

  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%)

출처 및 근거

ORD 기록
ord-51c56aceecb74afea22b3836069578dc
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183262B2

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