1-Bromo-2,6-dichlorobenzene → 2,6-Dichloro-2′-methyl-1,1′-biphenyl

HRID 412823

Reaction equation

HRID 412823 reaction equation
Br[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:9].[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH3:10]

Participants

5

Reactant 3

HCID 295681-Bromo-2,6-dichlorobenzeneHCID 62657Potassium Phosphate, TribasicHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 143454472,6-Dichloro-2′-methyl-1,1′-biphenylYield 92.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Bromo-2,6-dichlorobenzene (90 mg,-0.40 mmol) reacted with 2-methylphenylboronic acid (82 mg, 0.60 mmol) using 2/4 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and K3PO4 (254 mg, 1.20 mmol) in toluene at 100° C. to give the title compound (88 mg, 76%): 1H-NMR (400 MHz, CDCl3): δ 8.07 (d, 2H, J=8.07 Hz), 7.28-7.18 (m, 3H), 7.15 (t, 1H, J=8.13 Hz), 7.00 (d, 1H, J=7.25 Hz), 1.99 (s, 3H). 13C{1H}-NMR (125 MHz, CDCl3): δ 139.23, 136.91, 136.16, 135.09, 129.90, 129.04, 129.01, 128.39, 127.88, 125.81, 19.30. GC/MS(EI): (M+).

Workup

  1. customat 100° C.

Sources & evidence

ORD record
ord-b80c3729f67c41f0a0dd3eb1a2ecdae9
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Linked notes

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