Water → HCID 18350649, compound

HRID 430474Notes

Reaction equation

HRID 430474 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31]C)=[C:6]([C:8]2([CH2:11][C:12]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:13]([NH:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[C:21](=[O:22])[O:20][CH2:19]4)=[O:14])[CH2:10][CH2:9]2)[CH:7]=1.B(Br)(Br)Br.O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:31])=[C:6]([C:8]2([CH2:11][C:12]([OH:30])([C:26]([F:28])([F:27])[F:29])[C:13]([NH:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[C:21](=[O:22])[O:20][CH2:19]4)=[O:14])[CH2:9][CH2:10]2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 15463548HCID 15463548, compound

Product 1

HCID 18350649HCID 18350649, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

225 mg of 5-{3-[1-(5-fluoro-2-methoxyphenyl)-cyclopropyl]-2-hydroxy-2-trifluoromethyl-propionylamino}-phthalide is mixed in 4.5 ml of dichloromethane at 0° C. with 2.48 ml of a 1 molar solution of boron tribromide in dichloromethane. After 3 hours of stirring at 0° C., the mixture is added to water, extracted with ethyl acetate, the organic phase is dried (Na2SO4) and concentrated by evaporation. After the residue is triturated with hexane, the title compound is obtained in crystalline form, flash point 196-199° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic phase is dried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. customAfter the residue is triturated with hexane

Sources & evidence

ORD record
ord-3517deb82aef4c46ab640806c0304d76
Source dataset
uspto-grants-2001_11
Patent number
US06323199B1

Reaction notes

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