Hydrochloric Acid → HCID 69072914, compound

HRID 2099264Notes

Reaction equation

HRID 2099264 reaction equation
CC(C)([O-])C.[K+].[OH:7][CH:8]1[CH2:12][CH2:11][O:10][CH2:9]1.Br[CH2:14][C:15]1[C:16]([Cl:28])=[C:17]([CH:21]=[CH:22][C:23]=1[S:24]([CH3:27])(=[O:26])=[O:25])[C:18]([OH:20])=[O:19].Cl>CN(C=O)C>[Cl:28][C:16]1[C:15]([CH2:14][O:7][CH:8]2[CH2:12][CH2:11][O:10][CH2:9]2)=[C:23]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 99603-Furanol, tetrahydro-HCID 189403273-(Bromomethyl)-2-chloro-4-(methylsulfonyl)benzoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 69072914HCID 69072914, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-15 °C

Procedure

At 0° C., 25 ml of DMF and 3.25 g (28 mmol) of potassium tert-butoxide were initially charged and mixed with 2.5 g (27.5 mmol) of 3-hydroxytetrahydrofuran. The solution was cooled to −15° C., and 4.7 g (140 mmol) of 3-bromomethyl-2-chloro-4-methylsulfonylbenzoic acid were added. The mixture was then stirred at 15-20° C. for one hour. The reaction was poured into 45 g of ice/water, acidified with 2N HCl and extracted with EA. The organic phases were dried with MgSO4, filtered and concentrated. This gave 5.41 g of a viscous oil of a purity of about 66% according to HPLC. Yield about 60%

Workup

  1. extractionextracted with EA
  2. dry with materialThe organic phases were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1e7eda02e0e8415c8d203bb0cef1a8c2
Source dataset
uspto-grants-2009_08
Patent number
US07569519B2

Reaction notes

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