Nitric Acid → HCID 14867156, compound

HRID 973406Notes

Reaction equation

HRID 973406 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:19]=[CH:18][C:9]([C:10]([CH:12]([CH3:17])[CH2:13][C:14]([OH:16])=[O:15])=[O:11])=[CH:8][CH:7]=1>>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([CH:12]([CH3:17])[CH2:13][C:14]([OH:16])=[O:15])=[O:11])=[CH:18][C:19]=1[N+:1]([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 13695195HCID 13695195, compound

Product 1

HCID 14867156HCID 14867156, compoundYield 77%

Procedure

To 300 ml of fuming nitric acid was added by small portions 51 g of 3-(4-bromobenzoyl)butyric acid with stirring over 2 hours, during which the internal temperature of the reaction mixture was maintained at 10° to 20° C. The resulting mixture was poured into 1 liter of ice water and then extracted with chloroform. The chloroform layer was washed with water and concentrated. The residue was crystallized from water to give 46 g (77%) of 3-(4-bromo-3-nitrobenzoyl)butyric acid [Compound a; Compound (IV) wherein R3 =CH3 ].

Workup

  1. temperaturewas maintained at 10° to 20° C
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. concentrationconcentrated
  5. customThe residue was crystallized from water

Sources & evidence

ORD record
ord-b14622c6fb834acf997be7f1dc61ddbb
Source dataset
uspto-grants-1991_11
Patent number
US05063227

Reaction notes

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