Methanol → 1-Chloro-2-ethynyl-4-(trifluoromethyl)benzene

HRID 1865435Notes

Reaction equation

HRID 1865435 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]#[C:13][Si](C)(C)C.CO.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][C:3]=1[C:12]#[CH:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 69018463{[2-Chloro-5-(trifluoromethyl)phenyl]ethynyl}(trimethyl)silane

Product 1

HCID 117457731-Chloro-2-ethynyl-4-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the intermediate from step A (2.7 g, 10 mmol) in 10:1 MeOH:H2O (60 mL) was added potassium carbonate (2.76 g, 20 mmol). The reaction was stirred at room temperature for 15 minutes after which the mixture was poured into a pH 7-phosphate buffer and extracted with methylene chloride (3×). The combined organic layers were then dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting oil was used without further purification. 1H NMR (CDCl3, 500 MHz): 7.8 (d, J=1.9 Hz, 1H), 7.5 (m, 2H), 3.48 (s, 1H).

Workup

  1. extractionextracted with methylene chloride (3×)
  2. dry with materialThe combined organic layers were then dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was used without further purification

Sources & evidence

ORD record
ord-e8d40046e1ac43fc9ab30eb3f5202ed8
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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