Hydrochloric Acid → HCID 10376845, compound

HRID 1586344Notes

Reaction equation

HRID 1586344 reaction equation
[F:1][C:2]1([F:14])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([OH:13])=[O:12])[C:4]=2[O:3]1.C([Li])CCC.[Cl:20]C(Cl)(Cl)C(Cl)(Cl)Cl.Cl>O1CCCC1.CCCCCC>[Cl:20][C:7]1[C:5]2[O:6][C:2]([F:1])([F:14])[O:3][C:4]=2[C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6214HexachloroethaneHCID 27740672,2-Difluoro-1,3-dioxaindane-4-carboxylic acidHCID 178418339Butyllithium

Product 1

HCID 10376845HCID 10376845, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

7.5 g (0.038 mol) of 2,2-difluoro-1,3-benzodioxole-4-carboxylic acid, prepared according to the process described in European Application 0,333,658, are dissolved, with stirring and under an argon atmosphere, in 75 ml of dry tetrahydrofuran (THF). ml (0.081 mol) of n-butyllithium in solution in hexane are run in dropwise at -70° C. After stirring for 1 hour, 8.9 g (0.038 mol) of hexachloroethane in solution in 50 ml of dry tetrahydrofuran (THF) are run in. After 2 hours at -70° C., the temperature is allowed to return to 10° C. The reaction mixture is hydrolysed with 150 ml of ice-cold water and brought to a pH of approximately 1 by addition of 1N hydrochloric acid. The aqueous phase is extracted with ether, dried over magnesium sulphate and concentrated under vacuum. The solid is washed with heptane to give 3.7 g (0.016 mol) of 7-chloro-2,2-difluoro-1,3-benzodioxole-4-carboxylic acid (yield: 42%; melting point: 185° C.).

Workup

  1. dissolutionare dissolved
  2. customdropwise at -70° C
  3. waitAfter 2 hours at -70° C.
  4. customto return to 10° C
  5. extractionThe aqueous phase is extracted with ether
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under vacuum
  8. washThe solid is washed with heptane

Sources & evidence

ORD record
ord-17233b19b9334af382f9e6a9fb6aa25e
Source dataset
uspto-grants-1999_08
Patent number
US05945382

Reaction notes

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