Hydrogen Bromide → HCID 21459022, compound

HRID 274525Notes

Reaction equation

HRID 274525 reaction equation
Br.C([O:9][C:10]1[CH:27]=[CH:26][C:13]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[O:15])=[CH:12][C:11]=1[O:28][CH3:29])C1C=CC=CC=1>C(O)(=O)C>[OH:9][C:10]1[CH:27]=[CH:26][C:13]([C:14]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:20][CH:21]=2)=[O:15])=[CH:12][C:11]=1[O:28][CH3:29]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 21458986HCID 21458986, compound

Product 1

HCID 21459022HCID 21459022, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

70 ml. of 33 percent hydrobromic acid in acetic acid are added within 15 minutes at 10° to 20 g of 4-(benzyloxy)-3-methoxy-4'-(trifluoromethyl)benzophenone (dissolved in 150 ml of methylene chloride). After stirring at 20° for 1.5 hours, the reaction mixture is poured into 600 ml. of ice-water: the methylene chloride phase is separated and the aqueous phase is extracted twice more with 100 ml. of methylene chloride. The combined methylene chloride phases are washed with 600 ml of water, dried over sodium sulfate and evaporated. The residue is chromatographed on 150 g of silica gel with methylene chloride. After recrystallization from methylene chloride/hexane, there is obtained 4-hydroxy-3-methoxy-4'-(trifluoromethyl)benzophenone of melting point 97°.

Workup

  1. additionthe reaction mixture is poured into 600 ml
  2. customof ice-water: the methylene chloride phase is separated
  3. extractionthe aqueous phase is extracted twice more with 100 ml
  4. washThe combined methylene chloride phases are washed with 600 ml of water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue is chromatographed on 150 g of silica gel with methylene chloride
  8. customAfter recrystallization from methylene chloride/hexane

Sources & evidence

ORD record
ord-a3112595b7eb43b1abc927a5a9031c12
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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