Diethyl Ether → Benzoic acid, 3-fluoro-, methyl ester

HRID 444018

Reaction equation

HRID 444018 reaction equation
[CH2:1]([O:3]CC)C.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](Cl)=[O:11]>CO>[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([O:3][CH3:1])=[O:11]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 743763-Fluorobenzoyl chloride

Product 1

HCID 521184Benzoic acid, 3-fluoro-, methyl esterYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a 1-liter flask fitted with a stirrer, addition funnel, condenser, and drying tube containing diethyl ether (200 ml) and methanol (anhd.; 64 g,; 2.0 moles) is added dropwise m-fluorobenzoyl chloride (317 g,; 2.0 moles) at room temperature over a 3 hour period. Additional methanol (10 ml) is added and the reaction mixture is stirred at room temperature overnight. The reaction mixture is then filtered through a bed of silicic acid and the solvent removed under vacuum to afford 285 grams of methyl 3-fluorobenzoate (92.5% yield). This was identical to the product prepared in Example 2A.

Workup

  1. customTo a 1-liter flask fitted with a stirrer, addition funnel, condenser
  2. customdrying tube
  3. filtrationThe reaction mixture is then filtered through a bed of silicic acid
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-ee45d687180a4b51bdc9eb888ce635ca
Source dataset
uspto-grants-1981_04
Patent number
US04262152

Linked notes

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