2,6-Difluorobenzonitrile → HCID 67301337, compound

HRID 1015370Notes

Reaction equation

HRID 1015370 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]1.[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23](F)[C:20]=1[C:21]#[N:22].CC(C)([O-])C.[K+]>CN(C)C=O>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][O:12][C:23]2[CH:24]=[CH:25][CH:26]=[C:19]([F:18])[C:20]=2[C:21]#[N:22])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 746952,6-DifluorobenzonitrileHCID 23665647Potassium tert-butoxideHCID 67302009HCID 67302009, compound

Product 1

HCID 67301337HCID 67301337, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-(2,6-Difluorophenoxy)cyclohexylmethanol (100 mg; 0.4 mmol) and 2,6-difluorobenzonitrile were combined in 3 mL of dimethylformamide under nitrogen flow and chilled to 0° C. Potassium t-butoxide (56 mg; 1.2 mmol) was added in portions. Mixture warmed to room temperature. After 4 hours reaction was quenched with 3 mL of water and mixture was extracted with 3×8 mL of ethyl acetate. Combined organics were washed with 5×8 mL of water, once with brine and dried over MgSO4. Crude oil was purified via flash chromatography using 0-20% ethyl acetate in hexanes to give 95 mgs of title compound. (66% yield).

Workup

  1. temperatureMixture warmed to room temperature
  2. customAfter 4 hours reaction
  3. customwas quenched with 3 mL of water and mixture
  4. extractionwas extracted with 3×8 mL of ethyl acetate
  5. washCombined organics were washed with 5×8 mL of water, once with brine
  6. dry with materialdried over MgSO4
  7. customCrude oil was purified via flash chromatography

Sources & evidence

ORD record
ord-b7cdffbda9f94f14b11169d751976e7d
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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