Lithium iodide → 3-Cyano-5-(trifluoromethyl)benzoic acid

HRID 1640147노트

반응식

HRID 1640147 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:6]([O:8]C)=[O:7])#[N:2].[I-].[Li+]>N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)[C:6]([OH:8])=[O:7])#[N:2]

참가 물질

4

반응물 2

HCID 66321Lithium iodideHCID 58902345Methyl 3-cyano-5-(trifluoromethyl)benzoate

생성물 1

HCID 589022873-Cyano-5-(trifluoromethyl)benzoic acid수율 92.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A mixture of methyl 3-cyano-5-(trifluoromethyl)benzoate (2.67 g, 0.0105 mol) and lithium iodide (13 g, 0.070 mol) in pyridine (70 mL) was subjected to MWI for 30 min at 100° C. The mixture was concentrated and residue was extracted with EtOAc. The organic solutions were combined, washed with 1N HCl(, water and brine, dried over Na2SO4, filtered, and concentrated. The residue was redissolved in EtOAc, washed by 0.2N HCl and brine, dried and concentrated to give 3-cyano-5-(trifluoromethyl)benzoic acid (2.09 g. 92%). 1H NMR (400 MHz, d6-DMSO) δ: 8.58 (s, 1H), 8.55 (s, 1H), and 8.39 (s, 1H). LCMS: ES− 214.2.

후처리

  1. concentrationThe mixture was concentrated
  2. extractionresidue was extracted with EtOAc
  3. washwashed with 1N HCl(, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was redissolved in EtOAc
  8. washwashed by 0.2N HCl and brine
  9. customdried
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2d493aab6646432396e7457d3e105927
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110687B2

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