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

HRID 412796

반응식

HRID 412796 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:20](B(O)O)[CH2:21][CH2:22][CH3:23]>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].C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:20][CH2:21][CH2:22][CH3:23])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 20479Butylboronic AcidHCID 62657Potassium Phosphate, TribasicHCID 775951-Bromo-4-tert-butylbenzene

생성물 1

HCID 5241684-Tert-butyl-1-n-butylbenzene수율 92%

시약·촉매·용매 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

A 4 mL vial was charged with 4-tert-butylbromobenzene (213 mg, 1.00 mmol), Pd(dba)2 (5.8 mg, 0.01 mmol, 1 mol %), Ph5FcP(t-Bu)2 (14.2 mg, 0.02 mmol, 2 mol %), K3PO4 (430 mg, 2.02 mmol, powdered) and n-butylboronic acid (124 mg, 1.21 mmol). Anhydrous toluene (2 mL) and a stirring bar were added, and the vial was then sealed with a cap containing a PTFE septum and removed from the drybox. The reaction mixture was stirred at 100° C. for 2.5 h. After the starting aryl halide was consumed as determined by GC, the reaction solution was cooled to room temperature. The reaction solution was then adsorbed onto silica gel directly, and the product was isolated by eluting with ethyl acetate/hexanes to give 175 mg (92%) of 4-tert-butyl-1-n-butylbenzene as colorless oil. Kugelrohl distillation was used for further purification.

후처리

  1. customthe vial was then sealed with a cap
  2. customremoved from the drybox
  3. customAfter the 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-801f7212aa3d403ea1696374d672f356
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562989B2

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