3-Phenoxybenzyl alcohol → 1-(Bromomethyl)-3-phenoxybenzene

HRID 1253231Notes

Reaction equation

HRID 1253231 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Br)([Br:18])=O>C1(C)C=CC=CC=1.N1C=CC=CC=1>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][Br:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 262953-Phenoxybenzyl alcoholHCID 68176Thionyl bromide

Product 1

HCID 945441-(Bromomethyl)-3-phenoxybenzeneYield 81.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 1140TolueneSolvent3×

Procedure

A solution of 3-phenoxybenzyl alcohol (36.0 grams, 0.18 mole) in toluene (95 ml) was added dropwise during a thirty minute period to a stirred solution of thionyl bromide (50 grams, 0.24 mole), pyridine (0.5 gram) and toluene (175 ml) while maintaining the temperature below 30° C. After the addition was complete,the reaction mixture was heated at 50°-60° C. for two hours. Upon cooling, the reaction mixture was concentrated under reduced pressure leaving a residue. This residue was dissolved in toluene (200 ml) and washed with water (10×100 ml) until a neutral pH was obtained. The dried (magnesium sulfate) toluene layer was concentrated under reduced pressure leaving a residue. This residue was distilled yielding 38.5 grams of 3-phenoxybenzyl bromide, b.p. 120°-144° C./0.05 mmHg. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturewhile maintaining the temperature below 30° C
  2. additionAfter the addition
  3. temperaturewas heated at 50°-60° C. for two hours
  4. temperatureUpon cooling
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. customleaving a residue
  7. washwashed with water (10×100 ml) until a neutral pH
  8. customwas obtained
  9. dry with materialThe dried (magnesium sulfate) toluene layer
  10. concentrationwas concentrated under reduced pressure
  11. customleaving a residue
  12. distillationThis residue was distilled

Sources & evidence

ORD record
ord-69fb01d39f7f4424a92b50d176b82e6f
Source dataset
uspto-grants-1988_05
Patent number
US04748186

Reaction notes

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