Borane;tetrahydrofuran → (2-Iodo-5-(trifluoromethyl)phenyl)methanol

HRID 505268Notes

Reaction equation

HRID 505268 reaction equation
B.C1COCC1.[I:7][C:8]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:9]=1[C:10](O)=[O:11]>C1COCC1>[I:7][C:8]1[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][C:9]=1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 184515332-Iodo-5-(trifluoromethyl)benzoic acid2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-THF (11.0M solution in THF; 94 mL; 94 mmol) was added to a stirred solution of 2-iodo-5-(trifluoromethyl)benzoic acid (Intermediate 9, 2.97 g; 9.4 mmol) in THF (300 mL) at 0° C. under N2. The reaction was heated at reflux for 90 min and then carefully quenched with 6N HCl until no further gas evolution. The reaction was diluted with H2O (250 mL) and extracted with EtOAc (3×250 mL). The combined extracts were washed with brine (300 mL), dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (0-25% EtOAc/hexanes gradient) to afford [2-iodo-5-(trifluoromethyl)phenyl]methanol as a white solid. LCMS=285.0 (M−17)+. 1H NMR (CDCl3, 500 MHz): δ 7.97 (d, J=8.3 Hz, 1 H), 7.79 (s, 1 H), 7.28 (d, J=8.4 Hz, 1 H), 4.75 (s, 2 H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 90 min
  3. customcarefully quenched with 6N HCl until no further gas evolution
  4. additionThe reaction was diluted with H2O (250 mL)
  5. extractionextracted with EtOAc (3×250 mL)
  6. washThe combined extracts were washed with brine (300 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified by flash chromatography on silica gel (0-25% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-23c1ac6ac681465da7135c5ec2512b9a
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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