Tetrabutylammonium Fluoride → HCID 59164456, compound

HRID 906541Notes

Reaction equation

HRID 906541 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10]#[C:11][Si](C)(C)C)[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:6][C:5]=1[NH2:20].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10]#[CH:11])[C:7]([C:16]([F:18])([F:17])[F:19])=[CH:6][C:5]=1[NH2:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59164502HCID 59164502, compound

Product 1

HCID 59164456HCID 59164456, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-amino-4-trifluoromethyl-5-trimethylsilanylethynyl-benzoic acid methyl ester (1.65 g, 5.23 mmol) in THF (20 mL) was added a solution of TBAF in THF (1M, 10.5 mL, 2 equiv) and the resulting solution was stirred at r.t. for 10 min. The solvent was removed in vacuo and the crude oil was dissolved in AcOEt. The organic phase was washed with saturated NH4Cl and water, dried (Na2SO4) and concentrated in vacuo to afford a dark red oil. The crude product was purified by flash chromatography (EtOAc/hexanes (1:3)) to furnish 2-amino-5-ethynyl-4-trifluoromethyl-benzoic acid methyl ester (750 mg, 55%) as an orange oil. (ESI-MS: m/z 285.3 [M+CH3CN+H]+, rt 5.60 min).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe crude oil was dissolved in AcOEt
  3. washThe organic phase was washed with saturated NH4Cl and water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto afford a dark red oil
  7. customThe crude product was purified by flash chromatography (EtOAc/hexanes (1:3))

Sources & evidence

ORD record
ord-5cc52c573c2e4a239f1129b6bafbdeb7
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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