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

HRID 2214379Notes

Reaction equation

HRID 2214379 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].B(Br)(Br)Br.Cl.O>C(Cl)Cl>[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 962WaterHCID 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 6344DichloromethaneSolvent

Procedure

First, 5.4 g of N-[2-fluoro-5-(2-methoxyphenoxy)-4-nitrophenyl]acetamide was dissolved in 50 ml of methylene chloride, to which 4.7 g of boron tribromide was added under ice cooling. After stirring at the same temperature for 2 hours, concentrated hydrochloric acid was added, and the mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and then concentrated. The resulting crystals were washed with t-butyl methyl ether to give 3.2 g of N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide.

Workup

  1. additionwas added under ice cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. washThe resulting crystals were washed with t-butyl methyl ether

Sources & evidence

ORD record
ord-b506dc723be54a4992e71309059569bb
Source dataset
uspto-grants-2006_09
Patent number
US07109148B2

Reaction notes

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