Acetic Acid → 4-(Bromomethyl)-1-fluoro-2-phenoxybenzene

HRID 1702508Notes

Reaction equation

HRID 1702508 reaction equation
C1(O[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]=2)C=CC=CC=1.[BrH:23].C(O)(=O)C>O>[F:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][Br:23])=[CH:10][C:11]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 12922713HCID 12922713, compound

Product 1

HCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.7 g (0.05 mol) of 4-fluoro-3-phenoxy-benzyl phenyl ether, 50 ml of 32% strength aqueous hydrobromic acid and 60 ml of glacial acetic acid was heated to the reflux temperature for 10 hours, while stirring. The reaction mixture was then poured into 200 ml of water and extracted twice with 200 ml of methylene chloride each time. The combined methylene chloride phases were then extracted twice by shaking with 100 ml of 10% strength sodium hydroxide solution each time. The organic phase was subsequently dried over magnesium sulphate and the solvent was then stripped off under a waterpump vacuum. The residue was freed from the last residues of solvent by incipient distillation at a bath temperature of 60° C./3 mbars. 4-Fluoro-3-phenoxy-benzyl bromide was thus obtained as a viscous oil.

Workup

  1. temperaturewas heated to the reflux temperature for 10 hours
  2. extractionextracted twice with 200 ml of methylene chloride each time
  3. extractionThe combined methylene chloride phases were then extracted twice
  4. stirringby shaking with 100 ml of 10% strength sodium hydroxide solution each time
  5. dry with materialThe organic phase was subsequently dried over magnesium sulphate
  6. distillationThe residue was freed from the last residues of solvent by incipient distillation at a bath temperature of 60° C./3 mbars

Sources & evidence

ORD record
ord-e86101c5423b4540bd316bdaaac4a7f2
Source dataset
uspto-grants-1983_04
Patent number
US04381412

Reaction notes

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