Dimethylformamide → HCID 19917940, compound

HRID 1755837Notes

Reaction equation

HRID 1755837 reaction equation
Br[C:2]1[CH:22]=[CH:21][C:5]2[O:6][C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:8][C:4]=2[C:3]=1[F:23].C([Li])CCC.CN(C)[CH:31]=[O:32].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[F:23][C:3]1[C:4]2[O:8][C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:6][C:5]=2[CH:21]=[CH:22][C:2]=1[CH:31]=[O:32]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 19917895HCID 19917895, compoundHCID 178418339Butyllithium

Product 1

HCID 19917940HCID 19917940, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

5-Bromo-4-fluoro-2,2-diphenyl-1,3-benzodioxol (17.3 g) are dissolved in 150 ml of tetrahydrofuran, treated at -78° C. with 29.1 ml of a 0.6M solution of n-butyllithium in n-hexane and stirred at -78° C. for 15 minutes. Thereupon, 10 ml of dimethylformamide are added, after stirring for a further 15 minutes the mixture is treated with semi-saturated, aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried with magnesium sulphate and evaporated. The residue is crystallized from ethanol. After drying there are obtained 12.7 g of 4-fluoro-2,2-diphenyl-1,3-benzodioxol-5-carboxaldehyde as white crystals of m.p. 92°-94° C.

Workup

  1. stirringafter stirring for a further 15 minutes the mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried with magnesium sulphate
  4. customevaporated
  5. customThe residue is crystallized from ethanol
  6. customAfter drying there

Sources & evidence

ORD record
ord-c8f02ca7b1ee4517ba885a5bc6b6edc2
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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