Phenylboronic Acid → (1,1'-Biphenyl)-2-methanol

HRID 382105

반응식

HRID 382105 반응식
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[K+].Br[C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][OH:16]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[OH:16][CH2:15][C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 66827Phenylboronic AcidHCID 728502-Bromobenzyl alcoholHCID 522689Potassium Fluoride

생성물 1

HCID 76229(1,1'-Biphenyl)-2-methanol수율 83%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 27342152-(Di-tert-butylphosphino)biphenyl촉매

실험 절차

An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol %), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 2-bromobenzyl alcohol (187 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 153 mg (83%) of the title compound.

후처리

  1. customAn oven dried resealable Schlenk tube
  2. customwas evacuated
  3. customThe tube was evacuated
  4. additionwas added through a rubber septum
  5. customThe tube was sealed with a teflon screwcap
  6. customhad been completely consumed
  7. additionThe reaction mixture was then diluted with ether (30 mL)
  8. filtrationfiltered through celite
  9. concentrationconcentrated
  10. customThe crude material was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-599a316925a9439c902258f3220cb49b
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06307087B1

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