Water → HCID 17989205, compound

HRID 1443293Notes

Reaction equation

HRID 1443293 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4](F)[C:3]=1[O:10][CH3:11].C[Si](C)(C)[N-:14][Si](C)(C)C.[K+].O.S(=O)(=O)(O)O.[C:28]1([CH3:34])[CH:33]=CC=C[CH:29]=1>C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([C:28]([CH3:34])([CH3:33])[C:29]#[N:14])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

7

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 27736582-Chloro-6-fluoro-3-methylanisoleHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 17989205HCID 17989205, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
27 °C

Procedure

17.6 g (100.8 mmol) of 2-chloro-6-fluoro-3-methylanisole is dissolved in 880 ml of toluene. After 27.8 g (403.2 mmol) of isobutyric acid nitrile is added, 302.4 ml (151.2 mmol) of a 0.5 molar solution of potassium hexamethyl disilazide in toluene is added in drops within 40 minutes (temperature increase to 27° C.). After 19 days of stirring at room temperature, the batch is mixed with 300 ml of water and 400 ml of ethyl acetate and then acidified with 10% sulfuric acid to a pH of 4. The aqueous phase is shaken with 200 ml of ethyl acetate. The combined organic extracts are washed with water and twice with saturated NaCl solution and then dried. After spinning-in and chromatography on silica gel (mobile solvent: ethyl acetate/hexane), 12.01 g (53.4%) of the desired compound is obtained.

Workup

  1. washThe combined organic extracts are washed with water and twice with saturated NaCl solution
  2. customdried

Sources & evidence

ORD record
ord-ded1447c92d04addb7379d65b975a5aa
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

Loading…