Sulfuric Acid → HCID 17989205, compound

HRID 420628Notes

Reaction equation

HRID 420628 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].N(O)=O.[C:15](O)(=O)[CH:16]([CH3:18])[CH3:17].C[Si](C)(C)[N-:23][Si](C)(C)C.[K+].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[Cl:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([C:16]([CH3:18])([CH3:17])[C:15]#[N:23])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 27736582-Chloro-6-fluoro-3-methylanisoleHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86642296HCID 86642296, compound

Product 1

HCID 17989205HCID 17989205, compoundYield 53.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×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 nitrite 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 until a pH of 4 is reached. 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 ad 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 ad
  2. customthen dried

Sources & evidence

ORD record
ord-d1ea5f8dfa00471090a169f357309261
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

Loading…