Methyl iodide → HCID 18920212, compound

HRID 1483650Notes

Reaction equation

HRID 1483650 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[OH:12])[CH3:2].[C:14](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[O:12][CH3:14])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 22478444Ethyl 4-fluoro-2-hydroxybenzoate

Product 1

HCID 18920212HCID 18920212, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of compound 4 (19.9 g, 0.109 mol) in acetonitrile (200 mL) was added cesium carbonate (42.0 g, 0.129 mol). The resulting mixture was stirred at rt for 30 min. followed by addition of methyl iodide (13.5 mL, 0.218 mol). The resulting mixture was stirred at rt O/N and filtered through Celite. The solvent was removed under reduced pressure to give crude product 5 (20.0 g, 93%) and used in the next step without further purification. 1H NMR 400 MHz (CDCl3) δ: 7.81-7.78 (m, 1H), 6.60-6.58 (m, 2H), 4.38 (q, J=7.0 Hz, 2H), 3.82 (s, 3H), 1.39 (t, J=7.0 Hz, 3H); MS (ES) m/z: 199 (M+1)′.

Workup

  1. stirringThe resulting mixture was stirred at rt O/N
  2. filtrationfiltered through Celite
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7b5b42245e27412ab51ed67f578e6b14
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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