Potassium Carbonate → 3-Chloropropyl 4-(3-chloropropoxy)-2-fluorobenzoate

HRID 1710772Notes

Reaction equation

HRID 1710772 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Br[CH:13]([Cl:16])[CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:16][CH2:13][CH2:14][CH2:15][O:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([O:6][CH2:15][CH2:14][CH2:13][Cl:16])=[O:5])=[C:2]([F:1])[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 36872Propane, bromochloro-HCID 27833982-Fluoro-4-hydroxybenzoic Acid

Product 1

HCID 594574783-Chloropropyl 4-(3-chloropropoxy)-2-fluorobenzoateYield 155.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-fluoro-4-hydroxybenzoic acid (1 g, 6.41 mmol, 1 eq) is reacted with bromochloropropane (0.82 ml, 8.33 mmol, 1.3 eq) in the presence of potassium carbonate (1.77 g, 12.81 mmol, 2 eq) in methyl ethyl ketone (18 ml) at 80° C. overnight, filtered, washed with acetone and concentrated under vacuum to afford 2 g of 3-chloropropyl 4-(3-chloropropoxy)-2-fluorobenzoate i76.

Workup

  1. filtrationfiltered
  2. washwashed with acetone
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-90b9466997ac4e6f9f1bb9bee24a9acb
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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