2-Amino-4-fluorophenol → 5-Fluoro-2(3H)-benzoxazolone

HRID 1271682

Reaction equation

HRID 1271682 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=[O:2].[NH2:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[OH:21]>ClCCl>[F:20][C:18]1[CH:17]=[CH:16][C:15]2[O:21][C:1](=[O:2])[NH:13][C:14]=2[CH:19]=1

Participants

4

Reactant 2

HCID 27359172-Amino-4-fluorophenolHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 2872085-Fluoro-2(3H)-benzoxazoloneYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbonyl diimidazole (7.6 g) was added to a solution of 2-amino-4-fluorophenol (5 g, 39 mmol) in dichloromethane (0.100 ml). After 14 hours the solution was washed with 5M aqueous HCl, water, and dried over magnesium sulfate. The solution was filtered through a plug of silica and evaporated affording a white solid (4.0 g, 66%).

Workup

  1. washAfter 14 hours the solution was washed with 5M aqueous HCl, water
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe solution was filtered through a plug of silica
  4. customevaporated

Sources & evidence

ORD record
ord-4546198c3ac949d9ac091528485bf21a
Source dataset
uspto-grants-2007_04
Patent number
US07205408B2

Linked notes

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