Potassium Carbonate → 4-(1,3-Benzodioxol-5-ylmethoxy)-2-fluorobenzonitrile

HRID 1004314Notes

Reaction equation

HRID 1004314 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH2:17]1[O:27][C:26]2[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][C:19]=2[O:18]1>CN(C)C=O>[O:27]1[C:26]2[CH:25]=[CH:24][C:21]([CH2:22][O:10][C:8]3[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=3)=[CH:20][C:19]=2[O:18][CH2:17]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 108259694-(1,3-Benzodioxol-5-ylmethoxy)-2-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-fluoro-4-hydroxybenzonitrile (S. M. Kelly, Helv.Chim.Acta. 1984, Volume 67, P.1572-1579) (30 g), potassium carbonate (45.36 g) and 3,4-methylenedioxybenzyl chloride (42.65 g) in dimethylformamide (500 ml) was stirred at 90° C. for 2 hours. The reaction mixture was filtered and the filtrate evaporated. The residue was stirred with ethyl acetate (500 ml) and filtered affording the title compound (32.1 g) as a cream coloured solid, m.p. 139-140° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-1458e205fb784c0b9f96978bded5836e
Source dataset
uspto-grants-2000_04
Patent number
US06048893

Reaction notes

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