Tetrabutylammonium Fluoride → 5-Ethynyl-2-methylbenzamide

HRID 1473089Notes

Reaction equation

HRID 1473089 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][Si](C)(C)C)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:11]([C:8]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([CH:7]=1)[C:4]([NH2:6])=[O:5])#[CH:12]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 682828232-Methyl-5-((trimethylsilyl)ethynyl)benzamide

Product 1

HCID 866757225-Ethynyl-2-methylbenzamideYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methyl-5-((trimethylsilyl)ethynyl)benzamide (170) (0.190 g, 0.819 mmol) in THF (4 mL) at 0° C. was added 1.0 M solution TBAF in THF (0.5 mL). The mixture was then stirred under N2 at 0° C. for 10 minutes and then at room temperature for 3 hours. The resulting mixture was concentrated under reduced pressure then diluted with water. The resulting precipitate was collected by vacuum filtration to give the title compound (I71) (0.087 g, 67%); 1H NMR (400 MHz, d6-DMSO) δ 7.80 (s, 1H), 7.41 (m, 3H), 7.25 (d, J=7.7 Hz, 1H), 4.17 (s, 1H), 2.36 (s, 3H).

Workup

  1. waitat room temperature for 3 hours
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. additionthen diluted with water
  4. filtrationThe resulting precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-e57407ba5b884001b9a6c7243d6cf067
Source dataset
uspto-grants-2015_04
Patent number
US09012461B2

Reaction notes

Loading…