Boron tribromide → 4-Formyl-3-hydroxybenzonitrile

HRID 2090191Notes

Reaction equation

HRID 2090191 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-6a80239474dc49848057b0191be3871c
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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