Thionyl Chloride → HCID 21200435, compound

HRID 1870783Notes

Reaction equation

HRID 1870783 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:8][C:5]([CH2:6]O)=[C:4]([F:14])[CH:3]=1.S(Cl)([Cl:17])=O>O1CCCC1.N1C=CC=CC=1>[Cl:1][C:2]1[C:9]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:8][C:5]([CH2:6][Cl:17])=[C:4]([F:14])[CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 21200446HCID 21200446, compound

Product 1

HCID 21200435HCID 21200435, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

Then, 6.7 g of 4-chloro-2-fluoro-5-isopropoxybenzylalcohol was dissolved in 70 ml of tetrahydrofuran, to which 1 ml of pyridine was added, and the mixture was cooled to 5° C.. Then, 5 ml of thionyl chloride was slowly added dropwise at 5° to 10° C., and the mixture was stirred at 5° C. for 1.5 hours. After completion of the reaction, the reaction mixture was filtered to separate the precipitated crystals, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, which afforded 7.3 g of 4-chloro-2-fluoro-5-isopropoxybenzyl chloride.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered
  4. customto separate the precipitated crystals
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9317304f21b04bb49824c67504e10265
Source dataset
uspto-grants-2000_08
Patent number
US06100257

Reaction notes

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