Borane → (2-Amino-3-bromo-5-fluorophenyl)methanol

HRID 2079633Notes

Reaction equation

HRID 2079633 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].B>C1COCC1>[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([F:12])=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 6331BoraneHCID 27817032-Amino-3-bromo-5-fluorobenzoic acid

Product 1

HCID 53871442(2-Amino-3-bromo-5-fluorophenyl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0.5M suspension of 2-amino-3-bromo-5-fluorobenzoic acid in THF in an ice bath was slowly added borane (1.0M/THF, 3 eq). The reaction mixture was stirred at ambient temperature for 24 h. The mixture was recooled to 0° C. and quenched with methanol and concentrated to remove solvent. The residue was taken into ethyl acetate and organic phase was washed with water, saturated sodium bicarbonate, brine, dried over sodium sulfate and concentrated to give yellow solid in 90% yield. ES/MS m/z 220/222 (MH+).

Workup

  1. customwas recooled to 0° C.
  2. customquenched with methanol
  3. concentrationconcentrated
  4. customto remove solvent
  5. washwas washed with water, saturated sodium bicarbonate, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto give yellow solid in 90% yield

Sources & evidence

ORD record
ord-cde0f98ba44b4c2dbb93a34fe6e2f09d
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

Loading…