Methanol → 3-Hydroxy-8-nitrobenzo[c]chromen-6-one

HRID 1968458Notes

Reaction equation

HRID 1968458 reaction equation
CO[C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[C:11]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:12]=1[C:13]([O:15]C)=[O:14].B(Br)(Br)Br.CO>C(Cl)Cl>[OH:9][C:7]1[CH:8]=[C:3]2[C:4]([C:11]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:12]=3[C:13](=[O:14])[O:15]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 57990576Methyl 2-(2,4-dimethoxyphenyl)-5-nitrobenzoate

Product 1

HCID 579905963-Hydroxy-8-nitrobenzo[c]chromen-6-oneYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-(2,4-dimethoxyphenyl)-5-nitrobenzoate (Reference Compound No. 1-1-(1), 43.5 g, 137 mmol) in anhydrous methylene dichloride (250 mL) was cooled to −78° C., boron tribromide (96.2 g, 384 mmol) was added dropwise thereto, and then the mixture was stirred at room temperature for 1 hour. The mixture was cooled to −50° C. and methanol (300 mL) was added thereto. The precipitates were filtered with methanol to give the titled reference compound (18.0 g) as a yellow solid. (Yield 51%)

Workup

  1. temperatureThe mixture was cooled to −50° C.
  2. filtrationThe precipitates were filtered with methanol

Sources & evidence

ORD record
ord-b003564a66a7493f90a69a95587f2d9a
Source dataset
uspto-grants-2013_04
Patent number
US08426406B2

Reaction notes

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