Hydrochloric Acid → 6-Fluoro-2-(2-fluoro-4-iodo-phenylamino)-3-nitro-benzaldehyde

HRID 79039Notes

Reaction equation

HRID 79039 reaction equation
C[O:2][CH:3](OC)[C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=1[F:22].Cl>C1COCC1>[F:10][C:9]1[C:4]([CH:3]=[O:2])=[C:5]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=2[F:22])[C:6]([N+:11]([O-:13])=[O:12])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67083703HCID 67083703, compound

Product 1

HCID 866562386-Fluoro-2-(2-fluoro-4-iodo-phenylamino)-3-nitro-benzaldehydeYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (2-dimethoxymethyl-3-fluoro-6-nitro-phenyl)-(2-fluoro-4-iodo-phenyl)-amine (1.0 g, 2.22 mmol) in THF (10 ml) was added a solution of 4M HCl at room temperature. After 2 hours the THF was removed in vacuo and the residue diluted with water (20 ml) providing a precipitate. The solid precipitate was collected by filtration, washed with water and dried under vacuum to yield the title compound (864 mg, 96%). LCMS (Method B): RT=4.06 min, [M−H]−=403.

Workup

  1. customAfter 2 hours the THF was removed in vacuo
  2. additionthe residue diluted with water (20 ml)
  3. customproviding a precipitate
  4. filtrationThe solid precipitate was collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-4db5997a153f4b2da6b0faf29228c1a2
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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