Ethanol → Benzoic acid, 2,3,4-trifluoro-, ethyl ester

HRID 10274

Reaction equation

HRID 10274 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](Cl)(=O)[C:14](Cl)=O.C(O)C>ClCCl.CN(C)C=O>[CH2:13]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([F:12])=[C:10]([F:11])[C:2]=1[F:1])[CH3:14]

Participants

6

Reactant 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 3029322,3,4-Trifluorobenzoic acid

Product 1

HCID 594559Benzoic acid, 2,3,4-trifluoro-, ethyl esterYield 97.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,3,4-trifluorobenzoic acid (10.85 g, 61.6 mmol) in dichloromethane (100 mL) is added oxalyl chloride (13.5 mL, 154 mmol) and N,N-dimethylformamide (3 drops). After 45 minutes, the reaction mixture is concentrated under vacuum. The resulting residue is dissolved in dichloromethane (100 mL) and to this solution is added ethanol (18 mL, 310 mmol). After 30 minutes, the reaction mixture is diluted with dichloromethane and washed with saturated NaHCO3, water, and brine. The organic layer is dried over MgSO4, filtered, and the filtrate is concentrated to afford the title compound as an oil (12.23 g). 1H NMR (CDCl3): δ 7.93–7.67 (m, 1H), 7.09–6.96 (m, 1H), 4.39 (q, 2H), 1.40 (t, 3H).

Workup

  1. concentrationthe reaction mixture is concentrated under vacuum
  2. dissolutionThe resulting residue is dissolved in dichloromethane (100 mL) and to this solution
  3. waitAfter 30 minutes
  4. washwashed with saturated NaHCO3, water, and brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-1ce2e721306346368ed59e7d64aa7c46
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Linked notes

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