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

HRID 412797

Reaction equation

HRID 412797 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b0b34f4f058149808efdfe46009df2f8
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Linked notes

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