Allyl bromide → 1-(Allyloxy)-3,5-difluoro-2-nitrobenzene

HRID 574078Notes

Reaction equation

HRID 574078 reaction equation
[F:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.F[C:14]1[CH:15]=C(O)C=C(F)[C:19]=1[N+]([O-])=O.C(Br)C=C.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:9][C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[C:3]=1[N+:10]([O-:12])=[O:11])[CH:14]=[CH2:19]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 118195353,5-Difluoro-2-nitrophenolHCID 178437653,5-Difluoro-4-nitrophenol

Product 1

HCID 671197941-(Allyloxy)-3,5-difluoro-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3,5-difluoro-2-nitrophenol and 3,5-difluoro-4-nitrophenol (3.54 g, 20 mmol), allyl bromide (2.9 g, 24 mmol) and potassium carbonate (8.3 g, 60 mmol) in acetone (50 mL) was refluxed for 2 h. The progress of reaction was monitored by TLC. After completion, the reaction mixture was concentrated under reduced pressure at 25° C. The residue was diluted with water extracted with ether. The organic layer was washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure at 25° C. The residue obtained was purified by silica gel column chromatography (0-1% ethyl acetate-hexane) to yield 1-(allyloxy)-3,5-difluoro-2-nitrobenzene (934 mg). 1H-NMR (400 MHz, CD3OD): δ 4.72 (2H, d), 5.32 (1H, d J=10.8), 5.42 (1H, d, J=17.2), 5.98-6.02 (1H, m), 6.85 (1H, dt), 6.96 (1H, d).

Workup

  1. customThe progress of reaction
  2. concentrationAfter completion, the reaction mixture was concentrated under reduced pressure at 25° C
  3. additionThe residue was diluted with water
  4. extractionextracted with ether
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure at 25° C
  8. customThe residue obtained
  9. customwas purified by silica gel column chromatography (0-1% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-803b505211514cf285cb88de3791d2c1
Source dataset
uspto-grants-2015_05
Patent number
US09034861B2

Reaction notes

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