Boron tribromide → 4-Formyl-3-hydroxybenzonitrile

HRID 1951380Notes

Reaction equation

HRID 1951380 reaction equation
B(Br)(Br)Br.[CH:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[O:15]C)=[O:6].C(=O)(O)[O-].[Na+]>ClCCl>[CH:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[OH:15])=[O:6]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 166592514-Formyl-3-methoxybenzonitrile

Product 1

HCID 128136484-Formyl-3-hydroxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

100 ml of a boron tribromide solution in dichloromethane (1 M, 100 mmol) are added dropwise to a solution of 8 g (49.64 mmol) of 4-formyl-3-methoxybenzonitrile in 80 ml of anhydrous dichloromethane at −78° C. under an argon atmosphere. The reaction mixture is stirred at RT until the precursor has completely reacted (about 5 days). The reaction solution is then neutralized at 0° C. with saturated sodium bicarbonate solution. The phases are separated and the organic phase is washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 3:1). 4.5 g (61% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. customhas completely reacted (about 5 days)
  2. customThe phases are separated
  3. washthe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-a1b70a31174c43f397229b0692daefd6
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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