Nitric Acid → 2-Bromo-4-chloro-6-nitrophenol

HRID 1377535Notes

Reaction equation

HRID 1377535 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[N+:10]([O-])([OH:12])=[O:11]>C(O)(=O)C.C(OC(=O)C)(=O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[OH:9]

Participants

6

Reactant 2

HCID 944Nitric AcidHCID 696702-Bromo-4-chlorophenol

Product 1

HCID 2918712-Bromo-4-chloro-6-nitrophenolYield 80.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2-bromo-4-chloro-phenol (99.24 g, 480 mM) in acetic acid (110 ml) and acetic anhydride (125 ml) was cooled to -10° C. Within 1 hour a solution containing 100% nitric acid (33 ml) and acetic acid (40 ml) was added between -10° and -5° C., with stirring. The mixture was stirred for an additional 1.5 hours at 0°-5° C., then the suspension poured onto 300 g of ice in 700 ml of water and stirred for a further 0.5 hour. The solid was collected, washed, and dried to give 97.12 g (80.1%) of the title compound (mp 121°-2° C.).

Workup

  1. additionwas added between -10° and -5° C.
  2. stirringThe mixture was stirred for an additional 1.5 hours at 0°-5° C.
  3. stirringstirred for a further 0.5 hour
  4. customThe solid was collected
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-0e6e3a5d268b42bcb75c21950c55423a
Source dataset
uspto-grants-1997_09
Patent number
US05665737

Reaction notes

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