Ethyl Acetate → N-[5-fluoro-1-(o-hydroxyphenyl)-1H-benzotriazole-6-yl]-1-cyclohexene-1,2-dicarboximide

HRID 259747Notes

Reaction equation

HRID 259747 reaction equation
[F:1][C:2]1[C:18]([N:19]2[C:28](=[O:29])[C:23]3[CH2:24][CH2:25][CH2:26][CH2:27][C:22]=3[C:20]2=[O:21])=[CH:17][C:5]2[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15]C)[N:7]=[N:8][C:4]=2[CH:3]=1.B(Br)(Br)Br.C(OCC)(=O)C>C(Cl)Cl>[F:1][C:2]1[C:18]([N:19]2[C:20](=[O:21])[C:22]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=3[C:28]2=[O:29])=[CH:17][C:5]2[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[OH:15])[N:7]=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 15346068N-[5-fluoro-1-(o-methoxyphenyl)-1H-benzotriazol-6-yl]-1-cyclohexene-1,2-dicarboximide

Product 1

HCID 15346069N-[5-fluoro-1-(o-hydroxyphenyl)-1H-benzotriazole-6-yl]-1-cyclohexene-1,2-dicarboximide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of N-[5-fluoro-1-(o-methoxyphenyl)-1H -benzotriazol-6-yl]-1-cyclohexene-1,2-dicarboximide (1.00 g, 0.003 mol) in methylene chloride is slowly added to a one molar boron tribromide in methylene chloride solution (5 mL, 0.005 mol) at -20° C. The reaction mixture is stirred at room temperature overnight, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a tan solid. Flash column chromatography of the solid using silica gel and 2.5% to 10% ethyl acetate in methylene chloride solutions gives the title product as a white solid, mp 274°-275° C.

Workup

  1. washwashed sequentially with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain a tan solid

Sources & evidence

ORD record
ord-6cb4758f81c04dab8e6d5192c0eeaaf3
Source dataset
uspto-grants-1996_06
Patent number
US05523277

Reaction notes

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