Methyl 3-amino-2-chloro-5-fluoro-4-methylbenzoate → 2,3-Dichloro-5-fluoro-4-methylbenzoic acid

HRID 34580

Reaction equation

HRID 34580 reaction equation
N[C:2]1[C:3]([Cl:14])=[C:4]([CH:9]=[C:10]([F:13])[C:11]=1[CH3:12])[C:5]([O:7]C)=[O:6].N([O-])=O.[Na+].[ClH:19]>Cl.Cl[Cu]>[Cl:14][C:3]1[C:2]([Cl:19])=[C:11]([CH3:12])[C:10]([F:13])=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 13657452Methyl 3-amino-2-chloro-5-fluoro-4-methylbenzoateHCID 86602196HCID 86602196, compound

Product 1

HCID 136574412,3-Dichloro-5-fluoro-4-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 313Hydrochloric AcidSolvent

Procedure

8 g of methyl 3-amino-2-chloro-5-fluoro-4-methylbenzoate are diazotized with NaNO2 /HCl in aqueous solution. This diazonium salt solution is added dropwise to a solution of 4.1 g of CuCl in 16 ml of concentrated HCl. The mixture is then warmed until no further gas is formed. After cooling, the solid which has precipitated is separated off and taken up in 30 ml of 50% strength EtOH. After addition of 2.3 g of NaOH, the mixture is boiled for 1 hour. After cooling to room temperature, the mixture is acidified with HCl and the solid which has precipitated is isolated. Melting point: 179°-80°. Yield: 5.2 g.

Workup

  1. temperatureThe mixture is then warmed until no further gas
  2. customis formed
  3. temperatureAfter cooling
  4. customthe solid which has precipitated
  5. customis separated off
  6. additionAfter addition of 2.3 g of NaOH
  7. customthe solid which has precipitated
  8. customis isolated

Sources & evidence

ORD record
ord-b8e48d4c300a4eb88eedc02c00b64818
Source dataset
uspto-grants-1988_08
Patent number
US04762844

Linked notes

Loading…