1-Bromo-3-chloropropane → HCID 53363621, compound

HRID 2042533Notes

Reaction equation

HRID 2042533 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:15])[N:12]([CH3:14])[N:13]=2)=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][CH2:19][Cl:20].C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:20][CH2:19][CH2:18][CH2:17][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:15])[N:12]([CH3:14])[N:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 1359822716-(4-Hydroxyphenyl)-2-methyl-3(2H)-pyridazinone

Product 1

HCID 53363621HCID 53363621, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Phenol from step 3 (500 mg, 2.3 mmol), 3-bromo-1-chloropropane (720 mg, 4.6 mmol) and K2CO3 (950 mg) in CH3CN (25 mL) was stirred at reflux 20 h. The reaction was filtered and concentrated. The resulting oil was dissolved in Et2O, and washed with water, NaCl solution, dried (MgSO4) and concentrated. The product was triturated with Et2O-hexanes to yield 580 mg (91%) mp 186-187° C. 1H NMR (DMSO-d6) δ 2.2 (t, 2H), 3.7 (s, 3H), 3.8 (t, 2H), 4.15 (t, 2H), 7.0-7.1 (m, 3H), 7.8 (d, 2H), 8.0 (d, 1H). MS m/z=279 (M+H).

Workup

  1. temperatureat reflux 20 h
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. dissolutionThe resulting oil was dissolved in Et2O
  5. washwashed with water, NaCl solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe product was triturated with Et2O-hexanes
  9. customto yield 580 mg (91%) mp 186-187° C

Sources & evidence

ORD record
ord-4abdc1c673e24c0cb948f67a99faa7b0
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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