Benzene, 2-bromo-1,4-dimethyl- → 2,5-Dimethylbiphenyl

HRID 227871

반응식

HRID 227871 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:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[CH3:20]>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.C1COCC1>[CH3:20][C:14]1[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 3

HCID 11121Benzene, 2-bromo-1,4-dimethyl-HCID 66827Phenylboronic AcidHCID 522689Potassium Fluoride

생성물 1

HCID 5225062,5-Dimethylbiphenyl수율 82%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 27342152-(Di-tert-butylphosphino)biphenyl촉매HCID 8028Tetrahydrofuran용매

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, 0.020 mmol, 2.0 mol %), phenylboronic acid (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-bromo-p-xylene (0.138 mL, 1.0 mmol) were 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 149 mg (82%) of the title compound.

후처리

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

출처 및 근거

ORD 기록
ord-0fc96fb876c146b2816281e659bf6391
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560582B2

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