2-(2-Chlorobenzyloxy)-5-fluorobenzoic acid → 2-(2-Chlorobenzyloxy)-5-fluorobenzyl alcohol

HRID 1921867Notes

Reaction equation

HRID 1921867 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:7]=1[C:8](O)=[O:9]>C1COCC1>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:7]=1[CH2:8][OH:9]

Participants

3

Reactant 1

HCID 578643802-(2-Chlorobenzyloxy)-5-fluorobenzoic acid

Product 1

HCID 578643292-(2-Chlorobenzyloxy)-5-fluorobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.50 g (20 mmol) of 2-(2-chlorobenzyloxy)-5-fluorobenzoic acid are dissolved in 25 ml of THF, heated to reflux and then 20 ml of 1 M borane-dimethyl sulfide complex are added dropwise. The mixture is then cooled to room temperature and stirred at this temperature for 1 h. The solvent is distilled out in vacuo, and water is added to the residue. Acidification is then carried out cautiously (copious gas evolution) with 1 N hydrochloric acid. 1 N sodium hydroxide solution is then added to make slightly basic, and the aqueous phase is extracted three times with dichloromethane. The organic phases are dried over magnesium sulfate, filtered and washed with dichloromethane, and concentrated. Petroleum ether is added to the residue, and the crystals which have separated out are filtered off with suction and dried on a clay dish. 3.65 g (13.6 mmol, 68% of theory) of the title compound are obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. addition20 ml of 1 M borane-dimethyl sulfide complex are added dropwise
  4. distillationThe solvent is distilled out in vacuo, and water
  5. additionis added to the residue
  6. addition1 N sodium hydroxide solution is then added
  7. extractionthe aqueous phase is extracted three times with dichloromethane
  8. dry with materialThe organic phases are dried over magnesium sulfate
  9. filtrationfiltered
  10. washwashed with dichloromethane
  11. concentrationconcentrated
  12. additionPetroleum ether is added to the residue
  13. customthe crystals which have separated out
  14. filtrationare filtered off with suction
  15. customdried on a clay dish

Sources & evidence

ORD record
ord-de8e8218c3954fb991931097ea222757
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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