Oxalyl chloride → HCID 18350475, compound

HRID 430440Notes

Reaction equation

HRID 430440 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].[C:18](Cl)(=O)C(Cl)=O>CN(C)C=O.ClCCCl>[N+:1]([C:4]1[CH:12]=[C:11]([O:13][C:14]([F:15])([F:16])[F:17])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH3:18])=[O:7])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 183504392-Nitro-4-(trifluoromethoxy)benzoic acid

Product 1

HCID 18350475HCID 18350475, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

2-Nitro-4-trifluoromethoxybenzoic acid (4.7 g) was heated under reflux conditions for 2 hours with oxalyl chloride (1.95 ml) and 1,2-dichloroethane (25 ml) containing N,N-dimethylformamide (2 drops). The solvents were evaporated to dryness, the residue dissolved in drv dichloromethane and added to a solution of triethylamine (2.08 g) in dry methanol. After 2 days, the solvent was evaporated and the residue partitioned between dichloromethane and sodium bicarbonate solution. The organic phase was dried (magnesium sulphate), evaporated and the residue purified by chromatography, eluting with dichloromethane/hexane to give methyl 2-nitro-4-trifluoromethoxybenzoate (4.9 g) as a yellow liquid, NMR (CDCl3) 3.9(s,3H), 7.5(m,1H), 7.75(brs, 1H), 7.85(d,1H).

Workup

  1. customThe solvents were evaporated to dryness
  2. dissolutionthe residue dissolved in drv dichloromethane
  3. additionadded to a solution of triethylamine (2.08 g) in dry methanol
  4. customthe solvent was evaporated
  5. customthe residue partitioned between dichloromethane and sodium bicarbonate solution
  6. dry with materialThe organic phase was dried (magnesium sulphate)
  7. customevaporated
  8. customthe residue purified by chromatography
  9. washeluting with dichloromethane/hexane

Sources & evidence

ORD record
ord-c5c15a20b6ef4493a35308e20dbfd455
Source dataset
uspto-grants-2001_11
Patent number
US06323155B1

Reaction notes

Loading…