Water → Benzenamine, 4-chloro-2-fluoro-5-(2-propynyloxy)-

HRID 1903646Notes

Reaction equation

HRID 1903646 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([N+:12]([O-])=O)=[C:4]([F:15])[CH:3]=1.O>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([NH2:12])=[C:4]([F:15])[CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 13281441HCID 13281441, compound

Product 1

HCID 13272927Benzenamine, 4-chloro-2-fluoro-5-(2-propynyloxy)-Yield 72.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
90 °C

Procedure

A suspension of electrolytic iron powder (3.5 g) in a 5% aqueous acetic acid solution (5 ml) was heated to 90° C., and a solution of 4-chloro-2-fluoro-5-(2-propynyloxy)nitrobenzene (5.7 g) in acetic acid (40 ml) was dropwise added thereto at the same temperature. The resultant mixture was stirred at 90°-105° C. for 1 hour and allowed to cool to room temperature. Water (200 ml) was added thereto. Insoluble materials were filtered off, and the filtrate was neutralized, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated. The residue was washed with petroleum ether and carbon tetrachloride to give 3.6 g of 4-chloro-2-fluoro-5-(2-propynyloxy)aniline. M.P. 61.0°-61.5° C.

Workup

  1. temperatureto cool to room temperature
  2. filtrationInsoluble materials were filtered off
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washThe residue was washed with petroleum ether and carbon tetrachloride

Sources & evidence

ORD record
ord-305e59a15175432da4c889242c5c8a45
Source dataset
uspto-grants-1984_03
Patent number
US04437877

Reaction notes

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