Dimethylformamide → HCID 13393789, compound

HRID 2107721Notes

Reaction equation

HRID 2107721 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH:5]1[CH2:14][C:13](=O)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6]1.P(Cl)(Cl)([Cl:21])=O.CN(C)[CH:26]=[O:27]>>[Cl:21][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6][CH:5]([C:4]2[CH:16]=[CH:17][CH:18]=[C:2]([F:1])[CH:3]=2)[C:14]=1[CH:26]=[O:27]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 13393782HCID 13393782, compound

Product 1

HCID 13393789HCID 13393789, compound

Procedure

As in example 1, but using 10 g 3'-fluoro-flavanone, 100 ml dimethylformamide and 15 ml phosphorous oxychloride. Reaction time is two hours at 50° C. After hydrolysis a precipitate formed which is filtered, washed with water and dried over phosphorous pentoxyde. The residual solid is recrystallised in a mixture of ethanol and water and pure yellow crystalline 4-chloro-3'-fluoro-3-formyl-flav-3-ene is obtained; m.p. 97°-99° C.

Workup

  1. customReaction time
  2. customAfter hydrolysis a precipitate
  3. customformed which
  4. filtrationis filtered
  5. washwashed with water
  6. customdried over phosphorous pentoxyde
  7. customThe residual solid is recrystallised in a mixture of ethanol and water

Sources & evidence

ORD record
ord-d9ca488dc2ad48f986e2bfe6efd90079
Source dataset
uspto-grants-1990_06
Patent number
US04935441

Reaction notes

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