Ethanol → 3-Chloro-2,4,5-trifluorobenzoic acid ethyl ester

HRID 729359Notes

Reaction equation

HRID 729359 reaction equation
[Cl:1][C:2]1[C:3]([F:13])=[C:4]([CH:8]=[C:9]([F:12])[C:10]=1[F:11])[C:5]([OH:7])=[O:6].[C:14](Cl)(=O)[C:15](Cl)=O.C(O)C>ClCCl.CN(C)C=O>[CH2:14]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([F:12])[C:10]([F:11])=[C:2]([Cl:1])[C:3]=1[F:13])[CH3:15]

Participants

6

Reactant 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 27342693-Chloro-2,4,5-trifluorobenzoic Acid

Product 1

HCID 210411723-Chloro-2,4,5-trifluorobenzoic acid ethyl esterYield 100.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-chloro-2,4,5-trifluorobenzoic acid (Example 20, 4.90 g, 23.3 mmol) in dichloromethane (50 mL) is added oxalyl chloride (5.1 mL, 58.2 mmol) and N,N-dimethylformamide (1 drop). After 45 minutes, the reaction mixture is concentrated under vacuum. The resulting residue is dissolved in dichloromethane (50 mL) and treated with ethanol (10 mL, 172 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 (5.59 g). 1H NMR (CDCl3): δ 7.76-7.68 (m, 1H), 4.40 (q, 2H), 1.39 (t, 3H).

Workup

  1. concentrationthe reaction mixture is concentrated under vacuum
  2. dissolutionThe resulting residue is dissolved in dichloromethane (50 mL)
  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-61dad0f4443b4c12966d1b9d9d1f4672
Source dataset
uspto-grants-2009_09
Patent number
US07582627B2

Reaction notes

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