Hydrogen Bromide → HCID 14450977, compound

HRID 1781909Notes

Reaction equation

HRID 1781909 reaction equation
Br.C([O:9][C:10]1[CH:24]=[CH:23][C:13]([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])=[O:15])=[CH:12][C:11]=1[O:25][CH3:26])C1C=CC=CC=1>C(O)(=O)C>[F:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14](=[O:15])[C:13]1[CH:23]=[CH:24][C:10]([OH:9])=[C:11]([O:25][CH3:26])[CH:12]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 14450976HCID 14450976, compound

Product 1

HCID 14450977HCID 14450977, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

170 ml of 33 percent hydrobromic acid in glacial acetic acid are added at 20°-25° within 20 minutes to 42.4 g of 4-(benzyloxy)-2'-fluoro-3-methoxybenzophenone (dissolved in 450 ml of methylene chloride). After stirring at 20° for 1.5 hours, the reaction mixture is poured into 750 ml of ice-water; the methylene chloride phase is separated and the aqueous phase is extracted twice more with 200 ml of methylene chloride. The combined methylene chloride phases are washed with 1200 ml of water, dried over sodium sulfate and evaporated. In order to remove the resulting benzyl bromide, the oily residue is treated with hexane and decanted off. There is obtained 2'-fluoro-4-hydroxy-3-methoxybenzophenone as a yellowish oil which can be used directly in the subsequent reaction step.

Workup

  1. customthe methylene chloride phase is separated
  2. extractionthe aqueous phase is extracted twice more with 200 ml of methylene chloride
  3. washThe combined methylene chloride phases are washed with 1200 ml of water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customIn order to remove the resulting benzyl bromide
  7. additionthe oily residue is treated with hexane
  8. customdecanted off

Sources & evidence

ORD record
ord-a0b6669d0ef14f60878fe0cc42ec141a
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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