Hydrochloric Acid → 2,3,4-Trifluoro-5chlorobenzyl alcohol

HRID 260987Notes

Reaction equation

HRID 260987 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([F:15])=[C:6]([F:14])[C:7]([F:13])=[C:8]([CH:12]=1)[C:9](F)=[O:10].Cl>O1CCOCC1>[F:13][C:7]1[C:6]([F:14])=[C:5]([F:15])[C:4]([Cl:3])=[CH:12][C:8]=1[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 135650155-Chloro-2,3,4-trifluorobenzoyl fluoride

Product 1

HCID 135650212,3,4-Trifluoro-5chlorobenzyl alcoholYield 88.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

62 g of NaBH4 are initially introduced into 320 ml of dioxane. A solution of 319 g of 5-chloro-2,3,4-trifluorobenzoyl fluoride in 640 ml of dioxane is run into this, at the reflux temperature, over the course of 6 hours. After boiling under reflux for a further hour, the mixture is poured onto ice, the pH is adjusted to 1 with dilute hydrochloric acid, and the organic phase is extracted with methylene chloride and then distilled: 261 g of 2,3,4-trifluoro-5-chlorobenzyl alcohol of boiling point 109° C./12 mbar are obtained.

Workup

  1. customover the course of 6 hours
  2. temperatureunder reflux for a further hour
  3. additionthe mixture is poured onto ice
  4. extractionthe organic phase is extracted with methylene chloride
  5. distillationdistilled

Sources & evidence

ORD record
ord-598a992b0606442c81a74e664a029681
Source dataset
uspto-grants-1996_06
Patent number
US05530158

Reaction notes

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