Water → (2-Iodo-5-(trifluoromethyl)phenyl)methanol

HRID 1270793Notes

Reaction equation

HRID 1270793 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([I:12])=[C:7]([CH:11]=1)[C:8](O)=[O:9].O>C1COCC1>[F:13][C:2]([F:1])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([I:12])=[C:7]([CH:11]=1)[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 962Water2×HCID 184515332-Iodo-5-(trifluoromethyl)benzoic acid

Product 1

HCID 23160665(2-Iodo-5-(trifluoromethyl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Trifluoromethyl-2-iodobenzoic acid (50 g, 158 mmol) is dissolved in anhydrous THF (200 mL) and cooled in an ice-salt bath until the temperature reaches −5° C. Borane-THF complex is added dropwise as a 1.0 M solution in THF (350 mL, 350 mmol) at −5° C. After addition is complete, the reaction mixture is slowly warmed to room temperature and stirred for 12 hours. Water (40 mL) is carefully added dropwise (foaming) and the reaction mixture stirred for 30 minutes. Additional water (350 mL) is added and the mixture is concentrated by rotary evaporator to remove most of the THF. Additional water (250 mL) is added to form a precipitate, which is isolated by filtration to give 5-trifluoromethyl-2-iodobenzyl alcohol (m.p. 81–82° C.).

Workup

  1. temperaturecooled in an ice-salt bath until the temperature
  2. customreaches −5° C
  3. additionAfter addition
  4. stirringthe reaction mixture stirred for 30 minutes
  5. concentrationthe mixture is concentrated by rotary evaporator
  6. customto remove most of the THF
  7. additionAdditional water (250 mL) is added
  8. customto form a precipitate
  9. customwhich is isolated by filtration

Sources & evidence

ORD record
ord-8ca8f6f583564d88995f17938f87620d
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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