1,3-Dibromopropane → HCID 54351699, compound

HRID 27066Notes

Reaction equation

HRID 27066 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[CH:9]=[C:10]([CH:24]=[C:25]([CH3:28])[C:26]=1[OH:27])[C:11]([C:13]1[O:14][C:15]2[C:20]([C:21](=[O:23])[CH:22]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12].[Br:29][CH2:30][CH2:31][CH2:32]Br>CN(C)C=O>[Br:29][CH2:30][CH2:31][CH2:32][O:27][C:26]1[C:25]([CH3:28])=[CH:24][C:10]([C:11]([C:13]2[O:14][C:15]3[C:20]([C:21](=[O:23])[CH:22]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])=[CH:9][C:8]=1[CH3:7]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 64555162-(4-Hydroxy-3,5-dimethylbenzoyl)-4-benzopyrone

Product 1

HCID 54351699HCID 54351699, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

27.6 g (0.2 mol) of potassium carbonate was added to a solution of 29.4 g (0.1 mol) of 2-(3,5-dimethyl 4-hydroxy benzoyl) chromone in 150 ml of dimethyl formamide, 101 g (0.5 mol) of 1,3-dibromo propane was added and the admixture left at ambient temperature for 15 hours with constant agitation. The potassium bromide precipitate was filtered, the dimethyl formamide was concentrated in vacuo and the residue dissolved in 300 ml of water. Extraction was effected with 200 ml of methylene chloride, and precipitation was then effected by adding 200 ml of ether. The product was 36 g of 2-[4-(3-bromo propoxy) 3,5-dimethyl benzoyl] chromone.

Workup

  1. additionwas added
  2. filtrationThe potassium bromide precipitate was filtered
  3. concentrationthe dimethyl formamide was concentrated in vacuo
  4. dissolutionthe residue dissolved in 300 ml of water
  5. extractionExtraction
  6. customwas effected with 200 ml of methylene chloride, and precipitation
  7. additionby adding 200 ml of ether

Sources & evidence

ORD record
ord-27d8c0d2087641c8b0183c2e60b2269a
Source dataset
uspto-grants-1980_09
Patent number
US04220645

Reaction notes

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