Sodium Iodide → (5-Tert-butyl-2-methyl-4-thiocyanato-phenoxy)acetic acid methyl ester

HRID 1003859Notes

Reaction equation

HRID 1003859 reaction equation
[C:1]([C:5]1[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].[C:24]([O:27][CH2:28]Br)(=[O:26])[CH3:25]>C(#N)C>[CH3:28][O:27][C:24](=[O:26])[CH2:25][O:11][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]=1[CH3:12]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 68536Bromomethyl acetateHCID 105609555-tert-Butyl-2-methyl-4-thiocyanato-phenol

Product 1

HCID 54333600(5-Tert-butyl-2-methyl-4-thiocyanato-phenoxy)acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a round bottom flask (500 mL) equipped with a magnetic stirrer and condenser were added 2.0 g (9.0 mmol) of 5-tert-butyl-2-methyl-4-thiocyanato-phenol (prepared in Example GGG), cesium carbonate (5.88 g, 18.0 mmol), sodium iodide (4.8 g, 32.0 mmol), and acetonitrile (100 mL ). This suspension was heated to reflux for 30 minutes and bromomethyl acetate (1.76 mL, 18.0 mmol) was added via syringe. The reaction was refluxed overnight, cooled to room temperature, quenched with H2O and extracted with EtOAc. The organic layers were combined and dried (MgSO4). The solvent was evaporated and the residue dried under high vacuum to give the title compound. 1H NMR (CDCl3) δ 1.46 (s, 9 H), 2.26 (s, 3 H), 3.82 (s, 3 H), 4.68 (s, 2 H), 6.69 (s, 1 H), 7.52 (s, 1 H).

Workup

  1. customTo a round bottom flask (500 mL) equipped with a magnetic stirrer and condenser
  2. temperatureThis suspension was heated
  3. temperatureto reflux for 30 minutes
  4. temperatureThe reaction was refluxed overnight
  5. customquenched with H2O
  6. extractionextracted with EtOAc
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated
  9. customthe residue dried under high vacuum

Sources & evidence

ORD record
ord-1bc7b510c9a243c3853e766781a1ef23
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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