Isopropanol → HCID 67450353, compound

HRID 1505212Notes

Reaction equation

HRID 1505212 reaction equation
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].[CH:16]([OH:19])([CH3:18])[CH3:17]>>[CH:16]([O:19][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])([CH3:18])[CH3:17]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 5189732-Fluoro-4-(trifluoromethyl)benzonitrile

Product 1

HCID 67450353HCID 67450353, compound

Conditions

Temperature
50 °C

Procedure

The 2-fluoro-4-(trifluoromethyl)-benzonitrile (0.5 mL, 3.59 mmol) was added in small portion to a mixture of NaH 60% (4 mol eq) in isopropanol (10 mL). The reaction mixture was heated at 50° C. overnight. The solvent was distilled and water was added to the residue. The aqueous solution was extracted with EtOAc (3×25 mL) and the organic phases were evaporated at reduced pressure to give e as a white solid (0.84 g, quantitative yield). 1HNMR (DMSO, 200 MHz) δ 1.23 (s, 3H), 1.34 (s, 3H), 4.99 (m, 1H), 7.44 (m, 2H), 8.01 (d, 1H, J=8).

Workup

  1. distillationThe solvent was distilled
  2. additionwater was added to the residue
  3. extractionThe aqueous solution was extracted with EtOAc (3×25 mL)
  4. customthe organic phases were evaporated at reduced pressure

Sources & evidence

ORD record
ord-208f5f99f16e426dbec8c21757dda15c
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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