HCID 18434236, compound → HCID 18434233, compound

HRID 1636734Notes

Reaction equation

HRID 1636734 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[C:13]([O:17]C)=[CH:12][C:11]=2[F:19])=[O:9])=[CH:4][CH:3]=1>C(O)(=O)C.Br>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[C:13]([OH:17])=[CH:12][C:11]=2[F:19])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 18434236HCID 18434236, compound

Product 1

HCID 18434233HCID 18434233, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of 22.9 g of (4-bromo-phenyl)-(2,5-difluoro-4-methoxy-phenyl)-methanone in 140 ml of acetic acid and 100 ml of 62% aqueous HBr solution is boiled under reflux for 13 hrs., subsequently evaporated, re-evaporated with toluene and taken up in ethyl acetate. The inorganic phase is washed with saturated sodium hydrogen carbonate solution and 10% sodium chloride solution and dried. After crystallization from methylene chloride/ether/pentane there are obtained 20.8 g of (4-bromo-phenyl)-(2,5-difluoro-4-hydroxy-phenyl)-methanone.

Workup

  1. temperatureunder reflux for 13 hrs
  2. custom, subsequently evaporated
  3. customre-evaporated with toluene
  4. washThe inorganic phase is washed with saturated sodium hydrogen carbonate solution and 10% sodium chloride solution
  5. customdried
  6. customAfter crystallization from methylene chloride/ether/pentane there

Sources & evidence

ORD record
ord-d97fae9e487d4aab9cb5de446f28b24d
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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