Nitric Acid → 1-Bromo-2,4-dimethyl-5-nitrobenzene

HRID 2278396Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11]>>[Br:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]([CH3:8])=[CH:4][C:3]=1[CH3:9]

Participants

Reactant 2

HCID 944Nitric Acid

HCID 68503Benzene, 1-bromo-2,4-dimethyl-

Product 1

HCID 124743261-Bromo-2,4-dimethyl-5-nitrobenzene

Procedure

1-Bromo-2,4-dimethyl-benzene (9 g, 48.6 mmol) was added to HNO3 (100 mL, 60%) at rt. The mixture was stirred overnight at rt. The mixture was poured into ice-water and extracted with EtOAc. The organic phase was then dried over Na2SO4 and concentrated to give 1-bromo-2,4-dimethyl-5-nitro-benzene (6.5 g) which was used in the subsequent step without purification.

Workup

extractionextracted with EtOAc
dry with materialThe organic phase was then dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-daaf559146e54e96b3af4853c47b8756
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133180B2

Reaction notes

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