Allyl Alcohol → HCID 21075356, compound

HRID 1373752Notes

Reaction equation

HRID 1373752 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH:4]=[CH2:5].[Br:7][C:8]1[CH:13]=[CH:12][C:11](F)=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1>C1COCC1>[CH2:3]([O:6][C:11]1[CH:12]=[CH:13][C:8]([Br:7])=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16])[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 21075356HCID 21075356, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of anhydrous THF (200 mL) and 95% NaH (757 mg, 29.96 mmol) at 0° C. under N2 was added allyl alcohol (2.04 mL, 29.96 mmol) dropwise. After 0.5 hour, 4-bromo-1-fluoro-2-nitro-benzene (5.07 g, 23.04 mmol) was added dropwise. The reaction was warmed from 0° C. to room temperature under N2 overnight, and inorganic salt was filtered. The filtrate was concentrated with silica gel powder (20 g), and purified by flash chromatogrphy eluting with 10% ethyl acetate in hexanes (1 L) and 20% ethyl acetate in hexanes (1 L) to give the title compound (5.06 g, 85%). MS (DCI) m/z 257.35 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 4.65–4.70 (m, 2 H) 5.35 (m, 1 H) 5.48 (m, 1 H) 6.02 (m, 1 H) 6.97 (d, J=9.16 Hz, 1 H) 7.61 (dd, J=8.99, 2.54 Hz, 1 H) 7.97 (d, J=2.37 Hz, 1 H).

Workup

  1. temperatureThe reaction was warmed from 0° C. to room temperature under N2 overnight
  2. filtrationinorganic salt was filtered
  3. concentrationThe filtrate was concentrated with silica gel powder (20 g)
  4. custompurified by flash chromatogrphy
  5. washeluting with 10% ethyl acetate in hexanes (1 L) and 20% ethyl acetate in hexanes (1 L)

Sources & evidence

ORD record
ord-793f4f24a0e14d2abc2f1de22325bb3b
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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