Butylboronic Acid → 4-Tert-butyl-1-n-butylbenzene

HRID 412797

반응식

HRID 412797 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F-].[K+].[CH2:14](B(O)O)[CH2:15][CH2:16][CH3:17]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:14][CH2:15][CH2:16][CH3:17])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 20479Butylboronic AcidHCID 775951-Bromo-4-tert-butylbenzeneHCID 522689Potassium Fluoride

생성물 1

HCID 5241684-Tert-butyl-1-n-butylbenzene수율 115.6%

시약·촉매·용매 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

A 4 ml vial was charged with 4-tert-butylbromobenzene (1.00 mmol), Pd(dba)2 (0.01 mmol, 1 mol %), Ph5FcP(t-Bu)2 (0.02 mmol, 2 mol %), KF (2.02 mmol, powdered) and n-butylboronic acid (1.21 mmol). Anhydrous THF (2 ml) and a stirring bar were added, and the vial was sealed with a cap containing a PTFE septum and removed from the drybox. The reaction mixture was stirred at room temperature for 18 h. After a starting aryl halide was consumed as determined by GC, the reaction solution was cooled to room temperature. Then the reaction solution was adsorbed onto silica gel directly, and the product was isolated by eluting with ethyl acetate/hexanes to give 220 mg (98%) of 4-tert-butyl-1-n-butylbenzene as a colorless oil. Kugelrohl distillation was used for further purification.

후처리

  1. customthe vial was sealed with a cap
  2. customremoved from the drybox
  3. customAfter a starting aryl halide was consumed
  4. temperaturethe reaction solution was cooled to room temperature
  5. customthe product was isolated
  6. washby eluting with ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-b0b34f4f058149808efdfe46009df2f8
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562989B2

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