2-Bromoanisole → HCID 4176481, compound

HRID 412810Notes

Reaction equation

HRID 412810 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.[F-].[K+]>C1(C)C=CC=CC=1>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH3:10]

Participants

5

Reactant 3

HCID 113582-BromoanisoleHCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 4176481HCID 4176481, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Bromoanisole (187 mg, 1.00 mmol) reacted with 2-methylphenylboronic acid (150 mg, 1.10 mmol) using 1 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (116 mg, 2.0 mmol) in toluene at 100° C. to give the title compound (193 mg, 98%) as a colorless oil: 1H-NMR (400 MHz, CDCl3): δ 7.43 (t, 1H, J=8.2 Hz, aryl coupling J=1.75 Hz), 7.36-7.24 (m 5H), 7.10 (t, 1H, J=7.4 Hz, aryl coupling 0.91 Hz), 7.05 (d, 1H, J=8.2 Hz), 3.84 (s, 3H), 2.24 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 156.53, 138.58, 136.77, 130.95, 130.77, 129.95, 129.52, 128.51, 127.25, 125.40, 120.38, 110.56, 55.31, 19.89. GC/MS(EI): m/z 198 (M+). Anal. Calcd for C14H14O: C, 84.81; H, 7.12. Found: C, 84.97; H, 7.11.

Workup

  1. customat 100° C.

Sources & evidence

ORD record
ord-b9cbe864d7f8453f98966da03d5dad93
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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