Hydrochloric Acid → 2,2-Difluoro-benzo(1,3)dioxole-4-carbaldehyde

HRID 1614001Notes

Reaction equation

HRID 1614001 reaction equation
C([Li])CCC.CN(C)CCN(C)C.[F:14][C:15]1([F:24])[O:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16]1.CN([CH:28]=[O:29])C.Cl>C1(C)C=CC=CC=1>[CH:21]1[CH:20]=[C:18]2[O:19][C:15]([F:14])([F:24])[O:16][C:17]2=[C:23]([CH:28]=[O:29])[CH:22]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 741032,2-Difluoro-1,3-benzodioxoleHCID 178418339Butyllithium

Product 1

HCID 27369702,2-Difluoro-benzo(1,3)dioxole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

94.0 g (272 mmol) of n-butyllithium (18.5% in toluene) are added dropwise under a nitrogen atmosphere, at from -15° to -10° C., over a period of 1.5 hours, to 29.5 g (254 mmol) of N,N,N',N'-tetramethylethylenediamine and 40.0 g (253 mmol) of 2,2-difluoro-1,3-benzodioxole in 35 ml of toluene, an orange suspension being formed. 19.7 g (270 mmol) of DMF are then metered in at from -15° to -10° C. over a period of 1/2 hour. The pale yellow suspension is poured at +10° C. onto 346 g (1.105 mol) of 11.6% aqueous hydrochloric acid and the whole is stirred for 1/2 hour to complete the reaction. The aqueous phase is separated off and the organic phase is concentrated by evaporation in a vacuum rotary evaporator at 50° C./200 mbar under nitrogen to yield the desired product.

Workup

  1. customan orange suspension being formed
  2. customthe reaction
  3. customThe aqueous phase is separated off
  4. concentrationthe organic phase is concentrated by evaporation in a vacuum rotary evaporator at 50° C./200 mbar under nitrogen

Sources & evidence

ORD record
ord-dc03b8a0b1064bba98f1622bc2c05d52
Source dataset
uspto-grants-1993_03
Patent number
US05194628

Reaction notes

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