Dimethylformamide → HCID 54317890, compound

HRID 2251935Notes

Reaction equation

HRID 2251935 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br)=[CH:4][CH:3]=1.[K].[C:25]1([C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][O:27]1)=[O:26].C[N:36](C=O)C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:36]2[C:25](=[O:26])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]2=[O:27])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 17940764HCID 17940764, compoundHCID 67006573Potassium phthalide

Product 1

HCID 54317890HCID 54317890, compound

Procedure

9.0 g (23.6 mmol) 8,8-bis-(4-fluorophenyl)-octyl bromide and 4.7 g (25.0 mmol) phthalide potassium salt are stirred in 80 ml DMF for two hours at 70° C. After cooling, the mixture is concentrated and extracted with acetic acid ethyl ester and NaCl solution by shaking. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with petroleum ether/acetic acid ethyl ester (60/1 to 30/1): Yield 8.1 g (77%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated
  3. extractionextracted with acetic acid ethyl ester and NaCl solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is removed under vacuum
  6. customThe residue is chromatographically purified over silica gel with petroleum ether/acetic acid ethyl ester (60/1 to 30/1)

Sources & evidence

ORD record
ord-70b96236a0694c479deca503af201b1f
Source dataset
uspto-grants-2008_01
Patent number
US07320993B1

Reaction notes

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