1-Bromo-3,4-(methylenedioxy)benzene → HCID 18539333, compound

HRID 412813Notes

Reaction equation

HRID 412813 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:9][O:10][C:4]=2[CH:3]=1.[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.[F-].[K+]>C1(C)C=CC=CC=1>[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:9][O:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 758311-Bromo-3,4-(methylenedioxy)benzeneHCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 18539333HCID 18539333, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Bromo-1,2-(methylenedioxy)benzene (201 mg, 1.02 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, 2.00 mmol) in toluene at room temperature for 3 h to give the title compound (218 mg, 99%): 1H-NMR (300 MHz, CDCl3): δ 7.31-7.27 (m, 4H), 6.94-6.82 (m, 3H), 6.04 (s, 2H), 2.35 (s, 3H). 13C{1H}-NMR (125 MHz, CDCl3): δ 147.24, 146.39, 141.52, 135.84, 135.42, 130.26, 129.79, 127.10, 125.69, 122.44, 109.76, 107.98, 100.95, 20.45. GC/MS(EI): m/z 212 (M+), 181, 153. Anal. Calcd for C14H12O2: C, 79.23; H, 5.70. Found: C, 79.36; H, 5.73.

Workup

  1. customat room temperature
  2. customfor 3 h

Sources & evidence

ORD record
ord-f7f114f44f33406d8e1609756ccb5cf2
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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