Chlorodifluoromethane → HCID 11630445, compound

HRID 2263498Notes

Reaction equation

HRID 2263498 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[C:10]([F:16])=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:4]1)[CH3:2].[OH-].[Na+].Cl[CH:20]([F:22])[F:21]>C(O)(C)C>[F:21][CH:20]([F:22])[O:15][C:11]1[C:10]([F:16])=[C:9]([CH:6]2[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 57438793HCID 57438793, compound

Product 1

HCID 11630445HCID 11630445, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-(1-ethylpiperidin-4-yl)-2-fluorophenol (0.43 g, 1.9 mmol) ) in isopropanol (5 ml) and aqueous sodium hydroxide (30%, 5 ml) was added chlorodifluoromethane gas through a liner for 1 min. The mixture was heated to 65° C. and bubbling of chlorodifluoromethane was continued for an additional 30 min. Water (50 ml) was added and the mixture was extracted with ethylacetate (3×50 ml). The combined organic phases was dried (MgSO4), filtered and evaporated to dryness. MS m/z (rel. intensity, 70 eV) 273 (M+, 14), 272 (13), 259 (12), 258 (bp), 84 (13).

Workup

  1. custombubbling of chlorodifluoromethane
  2. additionWater (50 ml) was added
  3. extractionthe mixture was extracted with ethylacetate (3×50 ml)
  4. dry with materialThe combined organic phases was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-430018c9c4a5411f844a07e453a676f8
Source dataset
uspto-grants-2010_12
Patent number
US07851629B2

Reaction notes

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