2-Methoxy-4-nitrobenzaldehyde → 2-Hydroxy-4-nitrobenzaldehyde

HRID 339593Notes

Reaction equation

HRID 339593 reaction equation
C[O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]>C(Cl)Cl.B(Br)(Br)Br>[OH:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

4

Reactant 1

HCID 27595992-Methoxy-4-nitrobenzaldehyde

Product 1

HCID 755702-Hydroxy-4-nitrobenzaldehydeYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

Prepared as described in the Demethylation section above using 2-methoxy-4-nitrobenzaldehyde (1.0 g, 5.52 mmol) in dry DCM (25 ml) and BBr3 in DCM (1.0 M, 16 ml, 16 mmol) to give the title compound (0.70 g, 78%) as tan plates after recrystallisation from EtOH.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8c1625e8d0ab443193ea50f7d0b0a35b
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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