Hydrochloric Acid → Methyl [2-(5-acetylamino-2-chloro-4-fluorophenoxy)phenoxy]acetate

HRID 2214382Notes

Reaction equation

HRID 2214382 reaction equation
[ClH:1].[C:2]([NH:5][C:6]1[C:7]([F:26])=[CH:8][C:9](N)=[C:10]([CH:24]=1)[O:11][C:12]1[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=1[O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:4])[CH3:3].N([O-])=O.[Na+]>[Cu]Cl.O.COC(C)(C)C>[C:2]([NH:5][C:6]1[C:7]([F:26])=[CH:8][C:9]([Cl:1])=[C:10]([CH:24]=1)[O:11][C:12]1[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=1[O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:4])[CH3:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 21053882Methyl [2-(5-acetylamino-2-amino-4-fluorophenoxy)phenoxy]acetateHCID 23668193Sodium Nitrite

Product 1

HCID 21053881Methyl [2-(5-acetylamino-2-chloro-4-fluorophenoxy)phenoxy]acetate

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

To 30 ml of concentrated hydrochloric acid was added 2.0 g of methyl [2-(5-acetylamino-2-amino-4-fluorophenoxy)phenoxy]acetate, and the mixture was stirred at room temperature for 1 hour. Then, an aqueous solution consisting of 0.42 g of sodium nitrite and 3 ml of water was added under ice cooling. After stirring at the same temperature for 1 hour, 40 ml of t-butyl methyl ether was added and 0.85 g of copper (I) chloride was added. After stirring for 30 minutes, water was added, and the mixture was extracted with t-butyl methyl ether. The organic layer was washed with water, dried over magnesium sulfate, and then concentrated. The residue was subjected to column chromatography (eluent: hexane/ethyl acetate=2/1) to give 0.52 g of methyl [2-(5-acetylamino-2-chloro-4-fluorophenoxy)phenoxy]acetate.

Workup

  1. additionwas added under ice cooling
  2. stirringAfter stirring at the same temperature for 1 hour
  3. stirringAfter stirring for 30 minutes
  4. extractionthe mixture was extracted with t-butyl methyl ether
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8d13b9b4931241fca3d8b66507fe4dd7
Source dataset
uspto-grants-2006_09
Patent number
US07109148B2

Reaction notes

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