Ethanol → HCID 67301305, compound

HRID 1454365Notes

Reaction equation

HRID 1454365 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:7]=[C:8]([CH2:13][C@@H:14]([OH:18])[C:15]([OH:17])=[O:16])[CH:9]=[CH:10][C:11]=1[Br:12].[CH3:19][CH2:20]O>>[Br:5][C:6]1[CH:7]=[C:8]([CH2:13][C@@H:14]([OH:18])[C:15]([O:17][CH2:19][CH3:20])=[O:16])[CH:9]=[CH:10][C:11]=1[Br:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 67302267HCID 67302267, compound

Product 1

HCID 67301305HCID 67301305, compound

Conditions

Temperature
0 °C

Procedure

0.8 mL (10.9 mmol) thionyl chloride were added dropwise to a solution of 3.2 g (9.9 mmol) of (R)-3-(3,4-dibromo-phenyl)-2-hydroxy-propionic acid in 40 mL dry EtOH cooled to 0° C. and the reaction mixture was stirred for 1 h at RT. The reaction solution was evaporated down i.vac., the residue combined with 30 mL DCM and filtered to remove the insoluble precipitate. After the solvent had been eliminated the product was obtained as a viscous oil, which was further reacted without purification.

Workup

  1. customThe reaction solution was evaporated down i.vac
  2. filtrationfiltered
  3. customto remove the insoluble precipitate
  4. customwas obtained as a viscous oil, which
  5. customwas further reacted without purification

Sources & evidence

ORD record
ord-61d313f1c05c4e5ba6b4bf08f71bccd4
Source dataset
uspto-grants-2009_01
Patent number
US07479488B2

Reaction notes

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