1-Bromo-2-methylpropane → HCID 58423255, compound

HRID 1398020Notes

Reaction equation

HRID 1398020 reaction equation
[F:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Br[CH2:12][CH:13]([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>CC#N>[F:1][C:2]1[C:9]([O:10][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 196072232-Fluoro-3-hydroxybenzonitrile

Product 1

HCID 58423255HCID 58423255, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A 100 mL round bottom flask was charged with a magnetic stir bar, 2-fluoro-3-hydroxybenzonitrile (0.500 g, 3.65 mmol), MeCN (13.89 ml), 1-bromo-2-methylpropane (0.699 ml, 7.29 mmol), and K2CO3 (1.008 g, 7.29 mmol). The mixture was then placed in an oil bath and heated to 60° C. with stirring overnight. This mixture was then cooled to rt, filtered through a bed of Celite, and conc. In vacuo. The crude material was purified via silica gel chromatography (40 g) using ethyl acetate/hexanes (1:4) as eluent to afford pure 2-fluoro-3-isobutoxybenzonitrile (0.610 g, 87%) as a colorless oil. M/z 194.

Workup

  1. additionA 100 mL round bottom flask was charged with a magnetic stir bar
  2. customThe mixture was then placed in an oil bath
  3. temperatureThis mixture was then cooled to rt
  4. filtrationfiltered through a bed of Celite
  5. customThe crude material was purified via silica gel chromatography (40 g)

Sources & evidence

ORD record
ord-27bf82d8d6f847d5b3f0aacd42d2e5d9
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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