Nitric Acid → 3,5-Difluoro-4-nitrophenol

HRID 1527724Notes

Reaction equation

HRID 1527724 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.[N+:10]([O-])([OH:12])=[O:11]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[C:7]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 759283,5-Difluorophenol

Product 1

HCID 178437653,5-Difluoro-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-difluorophenol (10 g, 76.9 mmol) in CH2Cl2 at 0° Celsius was added 4.9 mL of 70% nitric acid dropwise. After addition was complete, the reaction was allowed to warm to room temperature and stirred for 1 hour. The reaction was poured into a separatory funnel and washed once with 750 mL water. The organic layer was dried with Na2SO4, filtered and concentrated to dryness. The resulting residue was purified via FCC to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 6.81-6.67 (m, 2H), 3.40 (bs, 1H).

Workup

  1. additionAfter addition
  2. additionThe reaction was poured into a separatory funnel
  3. washwashed once with 750 mL water
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe resulting residue was purified via FCC

Sources & evidence

ORD record
ord-681475cfcc954e0990353d08829e6661
Source dataset
uspto-grants-2015_07
Patent number
US09089569B2

Reaction notes

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