Hydrogen Bromide → {4-[3-Bromo-2,2-bis(hydroxymethyl)propoxy]phenyl}(phenyl)methanone

HRID 531396Notes

Reaction equation

HRID 531396 reaction equation
[OH:1][CH2:2][C:3]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])=[CH:11][CH:10]=2)[CH2:6][O:5][CH2:4]1.[BrH:23]>O>[Br:23][CH2:4][C:3]([CH2:6][OH:5])([CH2:2][OH:1])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 89906737(4-{[3-(Hydroxymethyl)oxetan-3-yl]methoxy}phenyl)(phenyl)methanone

Product 1

HCID 89907389{4-[3-Bromo-2,2-bis(hydroxymethyl)propoxy]phenyl}(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Suspend (4-{[3-(hydroxymethyl)oxetan-3-yl]methoxy}phenyl)(phenyl)methanone in a mixture of 48% aq. HBr and water and heat the mixture to reflux for 1 hour. Extract the product into dichloromethane, and evaporate the solvent, the solid residue may be recrystallised from ethanol to provide {4-[3-bromo-2,2-bis(hydroxymethyl)propoxy]phenyl}(phenyl)methanone.

Workup

  1. temperatureheat the mixture
  2. temperatureto reflux for 1 hour
  3. extractionExtract the product into dichloromethane
  4. customevaporate the solvent
  5. customthe solid residue may be recrystallised from ethanol

Sources & evidence

ORD record
ord-693fb41c2ad141b39f5477b97ee2c183
Source dataset
uspto-grants-2016_05
Patent number
US09353211B2

Reaction notes

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