Thionyl Chloride → HCID 57672390, compound

HRID 2101768Notes

Reaction equation

HRID 2101768 reaction equation
[CH:1]1([C:4]2[C:9]([C:10]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=3[F:18])=[CH:8][C:7]([CH2:19]O)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.S(Cl)([Cl:23])=O>C(Cl)Cl>[Cl:23][CH2:19][C:7]1[CH:8]=[C:9]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[F:18])[C:4]([CH:1]2[CH2:3][CH2:2]2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 57672481HCID 57672481, compound

Product 1

HCID 57672390HCID 57672390, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a dry, round bottom flask containing 13.4 (0.24 g, 0.88 mmol) under an argon atmosphere was added dry DCM (5 mL). The resulting homogeneous solution was cooled to 0° C. After 15 minutes, thionyl chloride (0.20 mL, 2.74 mmol) was added dropwise at 0° C. Upon complete addition of thionyl chloride, the mixture was allowed to warm to room temperature and for 16 hours. After 19 hours, the solvent was removed under reduced pressure. The crude material was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 15% EtOAc in hexanes) to yield a colorless oil 13.5 (0.13 g, 49% yield.) 1H NMR (400 MHz, CDCl3) δ ppm 7.36 (2H, dd, J=8.2, 2.0 Hz), 7.13 (1H, m), 6.98 (1H, d, J=8.2 Hz), 6.93 (2H, m), 4.62 (2H, s), 3.84 (3H, s), 1.87 (1H, m), 0.91 (2H, m), 0.7 (2H, m).

Workup

  1. temperatureto warm to room temperature and for 16 hours
  2. waitAfter 19 hours
  3. customthe solvent was removed under reduced pressure
  4. customThe crude material was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-16e382994f7a483199c92b8a2b10539d
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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