Dimethylformamide → HCID 13393785, compound

HRID 2107718Notes

Reaction equation

HRID 2107718 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]2=O.P(Cl)(Cl)([Cl:21])=O.CN(C)[CH:26]=[O:27]>>[Cl:21][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[O:8][CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]=1[CH:26]=[O:27]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 4169706HCID 4169706, compound

Product 1

HCID 13393785HCID 13393785, compound

Procedure

As in example 1, but using 10 g 6-fluoro-flavanone, 100 ml dimethylformamide and 15 ml phosphorous oxychloride. Reaction time is one hour and a half 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 hexane and pure yellow crystalline 4-chloro-6-fluoro-3-formyl-flav-3-ene is obtained; m.p. 74°-75° C.

Workup

  1. customReaction time
  2. customat 50° C
  3. customAfter hydrolysis a precipitate
  4. customformed which
  5. filtrationis filtered
  6. washwashed with water
  7. customdried over phosphorous pentoxyde
  8. customThe residual solid is recrystallised in hexane

Sources & evidence

ORD record
ord-999b1fb67a37413c8d117466ed3492d1
Source dataset
uspto-grants-1990_06
Patent number
US04935441

Reaction notes

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