Allyl bromide → HCID 53893713, compound

HRID 1154594Notes

Reaction equation

HRID 1154594 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[CH:5]=[CH:4][C:3]=1[OH:18].C([O-])([O-])=O.[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27].C(OC=CC)=CC>C1(OC2C=CC=CC=2)C=CC=CC=1.CCCCCC.CC(=O)CC>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[CH:5]=[C:4]([CH:25]=[CH:26][CH3:27])[C:3]=1[OH:18]

Participants

8

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 1383231-[(Prop-1-en-1-yl)oxy]prop-1-eneHCID 13015711HCID 13015711, compound

Product 1

HCID 53893713HCID 53893713, compound

Reagents, catalysts & solvents 3

HCID 6569Methyl Ethyl KetoneSolvent2×HCID 7583Diphenyl EtherSolventHCID 8058HexaneSolvent

Procedure

A mixture of 2,3-dichloro-4-(2-fluorobenzoyl)phenol (98 g., 0.343 mole), K2CO3 (94 g., 0.68 mole), allyl bromide (37 ml., 0.425 ml.) and 750 ml. of 2-butanone was heated at reflux for 4 hours. After cooling the 2-butanone was partially evaporated and the residue distributed between methylene chloride and aqueous NaCl. The organic layer was dried and evaporated to give 105 g. of the intermediate propenyl ether as a liquid. This material was dissolved in an equal volume of diphenyl ether and heated at 250° for 3.5 hours. The cooled reaction mixture was diluted with hexane and washed several times with 1N aqueous KOH. The combined aqueous washes were acidified with 6N HCl and the resulting mixture extracted with methylene chloride. The methylene chloride solution was dried (MgSO4) and evaporated to a residue. Trituration with hexane gave 73 g. of solid product, m.p. 83°-84° C.

Workup

  1. temperatureat reflux for 4 hours
  2. customwas partially evaporated
  3. customThe organic layer was dried
  4. customevaporated
  5. customto give 105 g
  6. temperatureheated at 250° for 3.5 hours
  7. customThe cooled reaction mixture
  8. washwashed several times with 1N aqueous KOH
  9. extractionthe resulting mixture extracted with methylene chloride
  10. dry with materialThe methylene chloride solution was dried (MgSO4)
  11. customevaporated to a residue
  12. customTrituration with hexane gave 73 g

Sources & evidence

ORD record
ord-5bfb100a0a7243d2b388e53b7e5170e7
Source dataset
uspto-grants-1984_12
Patent number
US04490384

Reaction notes

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