Isobutanol → HCID 66746823, compound

HRID 1467051Notes

Reaction equation

HRID 1467051 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][OH:4].[H-].[Na+].[N+:8]([C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([N+]([O-])=O)[C:12]=1[C:13]#[N:14])([O-:10])=[O:9]>C1COCC1>[CH2:3]([O:4][C:15]1[CH:16]=[CH:17][CH:18]=[C:11]([N+:8]([O-:10])=[O:9])[C:12]=1[C:13]#[N:14])[CH:2]([CH3:5])[CH3:1]

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 24758Sodium hydrideHCID 520718Dinitrobenzonitrile

Product 1

HCID 66746823HCID 66746823, compoundYield 149.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methylpropan-1-ol (9.6 mL, 0.104 mol) in anhydrous THF (200 mL) was added NaH (60% in mineral oil, 4.565 g, 0.114 mol) in small portions at 0° C. under N2. After it was stirred at room temperature for 30 min, the reaction mixture was cooled down to −70 C. and 2,6-dinitrobenzonitrile (20.0 g, 0.104 mol) was added portionwise. After the addition was complete, the reaction mixture was stirred at −70° C.—RT overnight, then poured into ice water (600 mL). The resultant precipitate was collected by filtration and rinsed with water, hexane, and air dried to provide 2-isobutoxy-6-nitrobenzonitrile as a light yellow solid (34.3 g, 100%). 1H NMR (400 MHz, DMSO-d6) δ 1.0 (d, J=6.8 Hz, 6H), 2.04-2.11 (m, 1H), 4.02 (d, J=6.8 Hz, 2H), 7.69-7.71 (m, 1H), 7.84-7.90 (m, 2H). MS 221 (MH+).

Workup

  1. temperaturethe reaction mixture was cooled down to −70 C
  2. additionAfter the addition
  3. stirringthe reaction mixture was stirred at −70° C.—RT overnight
  4. filtrationThe resultant precipitate was collected by filtration
  5. washrinsed with water, hexane, and air
  6. customdried

Sources & evidence

ORD record
ord-10a2b52b8a7b42db95f0428f15903957
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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