Borane → HCID 86671736, compound

HRID 594994Notes

Reaction equation

HRID 594994 reaction equation
[NH2:1][C:2]1[C:3]([F:13])=[C:4]([C:8]([F:12])=[C:9]([F:11])[CH:10]=1)[C:5](O)=[O:6].B>C1COCC1>[NH2:1][C:2]1[C:3]([F:13])=[C:4]([CH2:5][OH:6])[C:8]([F:12])=[C:9]([F:11])[CH:10]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 6056483-Amino-2,5,6-trifluorobenzoic acid

Product 1

HCID 86671736HCID 86671736, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-Amino-2,5,6-trifluoro benzoic acid (500 mg, 2.6 mmol) in THF (4 mL) was cooled to 0° C. (ice bath). Borane (2.5 eq., 1M in THF) was added dropwise over 20 min. The reaction was allowed to warm slowly to rt and stirred at rt for 18 h. The reaction was quenched by addition of saturated NH4Cl (aq) and extracted with EtOAc. The organic phase was washed with H2O then brine, dried (Na2SO4), filtered and concentrated in vacuo to give (3-amino-2,5,6-trifluorophenyl)methanol as a pale brown solid (425 mg, 92%)

Workup

  1. customThe reaction was quenched by addition of saturated NH4Cl (aq)
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with H2O
  4. dry with materialbrine, dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73f1d2ad2f3b43c7980c566e4e36c985
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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