3-Chloro-2-methyl-1-propene → 1,2-Difluoro-4-(2-methylallyloxy)benzene

HRID 445867Notes

Reaction equation

HRID 445867 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].Cl[CH2:11][C:12]([CH3:14])=[CH2:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:8][C:7]1[CH:6]=[CH:5][C:4]([O:9][CH2:13][C:12]([CH3:14])=[CH2:11])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 759273,4-Difluorophenol

Product 1

HCID 585667011,2-Difluoro-4-(2-methylallyloxy)benzeneYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3,4-difluorophenol (2 g, 15.37 mmol), 3-chloro-2-methylpropene (1.66 mL, 16.91 mmol), and potassium carbonate (3.2 g, 23.06 mmol) in DMF (10 mL) was stirred at 85° C. for 6 h. The mixture was filtered and the filtrate was evaporated to dryness. The residue was purified by flash column chromatography eluting with hexanes-EtOAc (2:1) to provide 1,2-difluoro-4-(2-methylallyloxy)benzene (731) (1.78 g, 63%). 1H NMR (400 MHz, CDCl3) δ 7.05 (q, J=9.5 Hz, 1H), 6.76-6.71 (m, 1H), 6.63-6.60 (m, 1H), 5.07 (s, 1H), 5.00 (s, 1H), 4.38 (s, 2H), 1.82 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was purified by flash column chromatography
  4. washeluting with hexanes-EtOAc (2:1)

Sources & evidence

ORD record
ord-df013501849e4052ba3181cd48010d13
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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