HCID 13127255, compound → HCID 13127246, compound

HRID 1702470Notes

Reaction equation

HRID 1702470 reaction equation
[F:1][C:2]([F:28])([C:24]([F:27])([F:26])[F:25])[C:3]([C:5]1[S:6][C:7]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:9]=1)=[O:4].[CH3:29][Mg]Br>O1CCCC1>[F:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[CH:9]=[C:5]([C:3]([CH3:29])([C:2]([F:1])([F:28])[C:24]([F:25])([F:26])[F:27])[OH:4])[S:6][C:7]=2[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 13127255HCID 13127255, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 13127246HCID 13127246, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-pentafluoropropionyl-4,5-bis(4-fluorophenyl)thiophene (5.83 g, 13.9 mmole) in 80 ml tetrahydrofuran was treated with 3 M methyl magnesium bromide (5.1 ml, 1.1 equiv.). After 3 hours, additional methyl magnesium bromide (2 ml) was added. After 4 hours total reaction time, the reaction was quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The combined organics were washed with brine, dried and concentrated in vacuo. Chromatography on silica gel gave the title compound as an oil (4.4 g).

Workup

  1. waitAfter 4 hours total reaction time
  2. customthe reaction was quenched with saturated aqueous NH4Cl
  3. extractionextracted with ethyl acetate
  4. washThe combined organics were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b4956dabc8c4153af457897fc698cde
Source dataset
uspto-grants-1983_04
Patent number
US04381311

Reaction notes

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