Potassium Phosphate, Tribasic → 2-methyl-4'-tert-butylbiphenyl

HRID 412814Notes

Reaction equation

HRID 412814 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].[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1>[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 775951-Bromo-4-tert-butylbenzeneHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 113680992-methyl-4'-tert-butylbiphenylYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-tert-butylbromobenzene (220 mg, 1.03 mmol) reacted with 2-methylphenylboronic acid (178 mg, 1.31 mmol) using 1 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and K3PO4 (424 mg, mmol) in toluene at 80° C. to give the title compound (223 mg, 97%) as a colorless oil: 1H-NMR (300 MHz, CDCl3): δ 7.49 (d, 2H, J=8.4 Hz), 7.34-7.30 (m, 6H), 2.36 (s, 3H), 1.44 (s, 9H). 13C{1H}-NMR (125 MHz, CDCl3): δ 149.50, 141.79, 138.88, 135.42, 130.26, 129.88, 128.81, 127.00, 125.69, 124.92, 34.51, 31.42, 20.58. GC/MS(EI): m/z (M+). Anal. Calcd for C17H20: C, 91.01; H, 8.99. Found: C, 90.72; H, 8.88.

Workup

  1. customat 80° C.

Sources & evidence

ORD record
ord-b09696e3373c4748b7875959f05864ad
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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