Hydrochloric Acid → N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide

HRID 1280366Notes

Reaction equation

HRID 1280366 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18]C)=[CH:4][C:3]=1[NH:20][C:21](=[O:23])[CH3:22].C(Cl)Cl.B(Br)(Br)Br.Cl>O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])=[CH:4][C:3]=1[NH:20][C:21](=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 25134Boron tribromideHCID 21933575N-[2-fluoro-5-(2-methoxyphenoxy)-4-nitrophenyl]acetamide

Product 1

HCID 21933568N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamideYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.4 g of N-[2-fluoro-5-(2-methoxyphenoxy)-4-nitrophenyl]acetamide was dissolved in 50 mol of methylene chloride, then, 4.7 g of boron tribromide was added under ice cooling. The mixture was stirred for 2 hours under the same temperature, conc. hydrochloric acid was added to the solution and the resulted mixture was poured into water, extracted with ethyl acetate, the organic layer was washed with water, dried over magnesium sulfate, concentrated, and the resulted crystal was washed with t-butyl methyl ether to obtain 3.2 g of N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide.

Workup

  1. additionwas added to the solution
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. washthe resulted crystal was washed with t-butyl methyl ether

Sources & evidence

ORD record
ord-e198d1827ba74b98bc75578a6bab17c0
Source dataset
uspto-grants-2002_09
Patent number
US06451740B2

Reaction notes

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