Water → HCID 67211302, compound

HRID 2274045Notes

Reaction equation

HRID 2274045 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]([F:15])([F:14])[F:13])=[C:7]([CH:10]=1)[C:8]#[N:9].S(Cl)([Cl:18])=O.O>C1(C)C=CC=CC=1>[Cl:18][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]([F:15])([F:14])[F:13])=[C:7]([CH:10]=1)[C:8]#[N:9]

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 67211153HCID 67211153, compound

Product 1

HCID 67211302HCID 67211302, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

5-(Hydroxymethyl)-2-(trifluoromethoxy)benzonitrile (0.150 g, 0.691 mmol) was taken up in toluene (2 mL) and thionyl chloride (0.303 mL, 4.14 mmol) was added. The mixture was heated at 75° C. for 15 min. Water was added and the mixture was extracted with hexanes (2×75 mL). The organics were treated with aqueous NaHCO3. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated to give the title compound as a colorless oil (120 mg). LCMS m/z=236.2 [M+H]+. 1H NMR (500 MHz, CDCl3) δ ppm 1.98 (s, 1H), 4.52 (s, 2H), 7.32-7.34 (m, 1H), 7.59-7.62 (m, 1H), 7.68 (s, 1H).

Workup

  1. extractionthe mixture was extracted with hexanes (2×75 mL)
  2. additionThe organics were treated with aqueous NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6c0202236a844b498acb2920efdf7473
Source dataset
uspto-grants-2015_09
Patent number
US09126932B2

Reaction notes

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