Nitric Acid → 2-Chloro-4-fluoro-6-nitrophenol

HRID 1456654Notes

Reaction equation

HRID 1456654 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[N+:10]([O-])([OH:12])=[O:11]>O.CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[OH:9]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 748142-Chloro-4-fluorophenol

Product 1

HCID 37278862-Chloro-4-fluoro-6-nitrophenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 2-Chloro-4-fluorophenol (25 g, 0.171 mol) in H2O (100 mL) and Et2O (300 mL) at 0° C. was added dropwise concentrated nitric acid (25 mL). After the addition was complete the reaction was warmed to rt and stirred for 3 hr. The layers were separated and the organic phase washed with 1:1 brine:H2O, brine, dried over MgSO4, filtered and concentrated in vacuo to a slurry. The slurry was diluted with hexane and the yellow solid collected and dried to provide 23.6 g of compound 711. ##STR90##

Workup

  1. additionAfter the addition
  2. customThe layers were separated
  3. washthe organic phase washed with 1:1 brine
  4. dry with materialH2O, brine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a slurry
  7. additionThe slurry was diluted with hexane
  8. customthe yellow solid collected
  9. customdried

Sources & evidence

ORD record
ord-a84a1d05b7ef4086a018f6692a7f89ed
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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