Thionyl Chloride → HCID 55204718, compound

HRID 2040564Notes

Reaction equation

HRID 2040564 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][C:7]=2[C:14]([F:17])([F:16])[F:15])[CH2:3][CH2:2]1.S(Cl)([Cl:20])=O>C1(C)C=CC=CC=1>[Cl:20][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[C:7]([C:14]([F:17])([F:16])[F:15])[CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 63320628HCID 63320628, compound

Product 1

HCID 55204718HCID 55204718, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of (4-(cyclopropylmethoxy)-3-(trifluoromethyl)phenyl)methanol (0.258 g, 1.454 mmol) in toluene (4 mL) was added thionyl chloride (0.637 mL, 8.72 mmol). The reaction was stirred at 75° C. for 1.5 h. The reaction mixture was poured into ice water and extracted with hexanes (twice). The combined extracts were washed with NaHCO3 (thrice), dried over MgSO4 and concentrated to give the title compound as a white solid (0.275 g). 1H NMR (400 MHz, CDCl3) δ ppm 0.36-0.43 (m, 2H), 0.59-0.67 (m, 2H), 1.21-1.34 (m, 1H), 3.95 (d, J=6.44 Hz, 2H), 4.56 (s, 2H), 6.95 (d, J=8.59 Hz, 1H), 7.48 (dd, J=8.53, 2.34 Hz, 1H), 7.58 (d, J=2.15 Hz, 1H).

Workup

  1. extractionextracted with hexanes (twice)
  2. washThe combined extracts were washed with NaHCO3 (thrice)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c7b7955444da4a32abc7eb0db1ab1fa0
Source dataset
uspto-grants-2013_11
Patent number
US08580841B2

Reaction notes

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