Hydrochloric Acid → (2-Iodo-5-(trifluoromethyl)phenyl)methanol

HRID 1994501Notes

Reaction equation

HRID 1994501 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+].Cl>C1COCC1.O>[I:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:12])([F:13])[F:11])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 716509062-Iodo-5-(trifluoromethyl)benzaldehyde

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

An alternative procedure is as follows: To a solution of 2-Iodo-5-(trifluoromethyl)benzaldehyde (EXAMPLE 80, Step A, 9 g) in THF (100 mL) and water (10 mL) at 0° C. was added NaBH4 (0.5 g). The reaction was stirred 30 minutes. To the reaction mixture was added dilute aqueous HCl (cautiously). The mixture was extracted with ether and the ether layer was washed with water, then brine. The ether layer was then dried over anhydrous MgSO4, filtered and concentrated. The material is chromatographed on SiO2 using a step gradient of 1:3 CH2Cl2/hexanes, then 1:1 CH2Cl2/hexanes, then 100% CH2Cl2 to afford [2-iodo-5-(trifluoromethyl)phenyl]methanol as a white solid.

Workup

  1. extractionThe mixture was extracted with ether
  2. washthe ether layer was washed with water
  3. dry with materialThe ether layer was then dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material is chromatographed on SiO2 using a step gradient of 1:3 CH2Cl2/hexanes

Sources & evidence

ORD record
ord-0e68aac6d87f4764bb14a7dd2824286c
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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