Ethyl Acetate → 3,4-Dihydroxy-5-nitrobenzaldehyde

HRID 924983Notes

Reaction equation

HRID 924983 reaction equation
[OH:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:13]C.B(Br)(Br)Br.CCOC(C)=O>C(Cl)Cl>[OH:13][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=1[OH:1])[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 811345-Nitrovanillin

Product 1

HCID 57489573,4-Dihydroxy-5-nitrobenzaldehydeYield 64.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-3-methoxy-5-nitrobenzaldehyde (2.0 g, 10.15 mmol) in anhydrous CH2Cl2 (10 mL) was added boron tribromide (4 mL) at 0° C. Reaction was warmed to room temperature and stirred for 2 hour under N2. Followed a standard aqueous/EtOAc workup. The residue was purified by silica gel column chromatography (1.2 mg, yield: 64.6%).

Workup

  1. customReaction
  2. customThe residue was purified by silica gel column chromatography (1.2 mg, yield: 64.6%)

Sources & evidence

ORD record
ord-8c0065e00b6e4fe295727ec4e987e1ec
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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