Hydrogen Bromide → 4,5-Dihydroxy-2-nitrobenzaldehyde

HRID 1982218

Reaction equation

ClC[O:3][C:4]1[C:5]([OH:15])=[CH:6][C:7]([N+:12]([O-:14])=[O:13])=[C:8]([CH:11]=1)[CH:9]=[O:10].Br>>[OH:15][C:5]1[C:4]([OH:3])=[CH:11][C:8]([CH:9]=[O:10])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 114247525-Chloromethoxy-4-hydroxy-2-nitrobenzaldehyde

Product 1

HCID 37823444,5-Dihydroxy-2-nitrobenzaldehydeYield 93%

Procedure

5-Chloromethoxy-4-hydroxy-2-nitrobenzaldehyde (10) (3 g; 0.013 mol) is stirred at 23° C. with 15 ml 48% HBr for two days. The precipitate is removed by filtration, and washed well with H2O, giving 2.2 g (93%) of 4,5-dihydroxy-2-nitrobenzaldehyde (1). The remainder of the product is isolated by ether extraction of the filtrate. Drying the combined ether extracts over Na2SO4, filtering, and removing the ether at reduced pressure, gives the remaining 0.17 g (7%) of (1): mp 201°-203° C.; mass spectrum, m/e 183 (M+); 1HNMR (d6 -Me2CO) δ10.59 (br s,2H), δ10.2(s,1H), δ7.6(s,1H), δ7.3(s,1H).

Workup

customThe precipitate is removed by filtration
washwashed well with H2O

Sources & evidence

ORD record: ord-152d51ab762c4de391e6b7d9effed8ea
Source dataset: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04595765

Linked notes

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