Chlorodifluoromethane → HCID 59769973, compound

HRID 2218636Notes

Reaction equation

HRID 2218636 reaction equation
[OH-].[K+].[CH:3]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[C:8](=[CH:18][C:19]3[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl[CH:27]([F:29])[F:28]>C(O)(C)C>[F:28][CH:27]([F:29])[O:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH:18]=[C:8]1[C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[CH2:11][CH2:12][C:13]2[CH:3]=[CH:4][CH:5]=[CH:6][C:7]1=2

Participants

5

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 14797Potassium HydroxideHCID 59770021HCID 59770021, compound

Product 1

HCID 59769973HCID 59769973, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Add pellets of KOH (376 mg, 6.7 mmol) to a solution of 3-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenol (200 mg, 0.67 mmol) in isopropanol (10 mL). Bubble chlorodifluoromethane (Freon 22) slowly into the reaction mixture for 2 h. Concentrate the reaction mixture, and take the residue up in 1N HCl. Extract into ethyl acetate, dry organics (MgSO4), filter, and concentrate to a milky tan oil containing the title compound. Purify via silica gel chromatography (1:20 ethyl acetate:hexanes) to afford 108 mg (20%) of a white solid, mp 91.3° C. 1H NMR (CDCl3) δ 2.66-3.56 (br m, 4H), 6.12 (t, 1H, J=80 Hz), 6.55-7.43 (m, 13H); MS (EI) 348. HPLC shows 97% purity.

Workup

  1. concentrationConcentrate the reaction mixture
  2. extractionExtract into ethyl acetate, dry organics (MgSO4)
  3. filtrationfilter
  4. concentrationconcentrate to a milky tan oil
  5. additioncontaining the title compound
  6. customPurify via silica gel chromatography (1:20 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-10f746bf07ff41e0b9900cc702355ac9
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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