Cesium carbonate → HCID 118452708, compound

HRID 1773218Notes

Reaction equation

HRID 1773218 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:18][C:19]#[N:20]>CC#N>[CH:4]([C:3]1[CH:6]=[CH:7][C:8]([CH3:10])=[CH:9][C:2]=1[O:1][CH2:18][C:19]#[N:20])=[O:5]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 612002-Hydroxy-4-methylbenzaldehyde

Product 1

HCID 118452708HCID 118452708, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-hydroxy-4-methylbenzaldehyde (12 g, 88 mmol) in 432 mL of CH3CN was added Cs2CO3 (34.5 g, 106 mmol) followed by 2-bromoacetonitrile (6.75 mL, 97 mmol), After the mixture was stirred at room temperature for 6 hr, the mixture was filtered through Celite to remove solid, washed with DCM, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel flash chromatography, 100% Heptane-20% Ethyl Acetate/80% Heptane) to give a white solid, 2-(2-formyl-5-methylphenoxy)acetonitrile (14.2 g). LCMS retention time=1.06 minutes (LC method 3); MS (m+1)=175.8. 1H NMR (400 MHz, DMSO-d6) δ 2.41 (s, 3H), 5.33 (s, 2H), 7.05 (d, J=7.8 Hz, 1H), 7.20 (s, 1H), 7.68 (s, 1H), 10.26 (d, J=0.8 Hz, 1H).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. customto remove solid
  3. washwashed with DCM
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel flash chromatography, 100% Heptane-20% Ethyl Acetate/80% Heptane)

Sources & evidence

ORD record
ord-9c8a1f2793b84d7699ecc71150fbd192
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Reaction notes

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