Borane → (4-Bromo-2-nitrophenyl)methanol

HRID 2079637Notes

Reaction equation

HRID 2079637 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.B>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 37744674-Bromo-2-nitrobenzoic acid

Product 1

HCID 15906236(4-Bromo-2-nitrophenyl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0.5M suspension of 4-bromo-2-nitrobenzoic acid in THF in an ice bath was slowly added borane (1.0M/THF, 4 eq). The reaction mixture was stirred at ambient temperature for 48 h. LCMS showed the reaction was complete. 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 95% yield.

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 95% yield

Sources & evidence

ORD record
ord-d17b9ee9dcab4304b052a84cc20ece92
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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