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

HRID 412796

反応式

HRID 412796 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 5241684-Tert-butyl-1-n-butylbenzene収率 92%

試薬・触媒・溶媒 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-801f7212aa3d403ea1696374d672f356
出典データセット
uspto-grants-2003_05
特許番号
US06562989B2

関連ノート

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