1,3-Dichloroacetone → HCID 23657702, compound

HRID 2220582Notes

Reaction equation

HRID 2220582 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[Br:7][C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:9]=1[CH:10]=O.Cl[CH2:18][C:19]([CH2:21]Cl)=[O:20]>CC(=O)CC>[Br:7][C:8]1[C:9]2[CH:10]=[C:18]([C:19]([C:21]3[O:4][C:1]4[CH:13]=[CH:12][CH:9]=[C:8]([Br:7])[C:15]=4[CH:14]=3)=[O:20])[O:16][C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 11430Potassium CarbonateHCID 119547682-Bromo-6-hydroxybenzaldehyde

Product 1

HCID 23657702HCID 23657702, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

Dried K2CO3 (7g, 50.1 mmol) was added to a solution of 2-bromo-6-hydroxybenzaldehyde (80) (6.57 g, 32.3 mmol) in dry butanone (35 mL). The suspension was refluxed for 30 min and cooled to room temperature. A solution of 1,3-dichloroacetone (3 g, 24.23 mmol) in 5 mL of dry butanone was added. The reaction mixture was refluxed for 4 hours, cooled down, filtered through a pad of Celite (2 cm) and concentrated. A dark residue was recrystallized from CHCl3 to give 82 as brown solid (5.05 g, 76%): mp 223-225° C. 1H NMR (DMSO-d6) δ8.10 (s, 2H), 7.92 (d, J=8.2 Hz, 2H), 7.70 (d, J=7.7 Hz, 2H), 7.57 (dd, J=8.2, 7.7 Hz, 2H). HPLC (method B) tR 9.83 min (100.00 area %). Anal. (C17H8Br2O3) C, H, Br.

Workup

  1. temperatureThe suspension was refluxed for 30 min
  2. temperatureThe reaction mixture was refluxed for 4 hours
  3. temperaturecooled down
  4. filtrationfiltered through a pad of Celite (2 cm)
  5. concentrationconcentrated
  6. customA dark residue was recrystallized from CHCl3

Sources & evidence

ORD record
ord-9882d70ba0e547e2a199bd491f0c6c79
Source dataset
uspto-grants-2008_08
Patent number
US07417158B2

Reaction notes

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