HCID 20286060, compound → HCID 54371081, compound

HRID 127124Notes

Reaction equation

HRID 127124 reaction equation
[F:1][C:2]1[C:20]([F:21])=[C:19]([O:22][CH3:23])[C:18]([F:24])=[C:17]([F:25])[C:3]=1[C:4](=[O:16])[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[O:7]1>C(O)(=O)C>[F:1][C:2]1[C:20]([F:21])=[C:19]([O:22][CH3:23])[C:18]([F:24])=[C:17]([F:25])[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[O:7]1

Participants

3

Reactant 1

HCID 20286060HCID 20286060, compound

Product 1

HCID 54371081HCID 54371081, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 3 gm (8 mmol) of 3-(2',3',5',6'-tetrafluoro-4'-methoxyphenacyl)phthalide in 40 ml of glacial acetic acid was heated and stirred at 55°-60° C., and 3 gm of molecular bromine in 20 ml of glacial acetic acid was added dropwise. The colorless solution of the α-brominated starting material was thereafter added to 260 ml of ice cold water with vigorous stirring. The white precipitate was filtered and dried, dissolved in 150 ml of methylene chloride and refluxed for 2 hours in the presence of 3 ml of triethylamine. Dilute acid washing, followed by concentration and recrystallization from ethanol gave 1.1 gm (45%) of 3-(2',3',5',6'-tetrafluoro-4'-methoxyphenacylidene)phthalide, mp 199°-200° C.

Workup

  1. temperaturewas heated
  2. filtrationThe white precipitate was filtered
  3. customdried
  4. dissolutiondissolved in 150 ml of methylene chloride
  5. temperaturerefluxed for 2 hours in the presence of 3 ml of triethylamine
  6. additionDilute acid
  7. washwashing
  8. concentrationfollowed by concentration and recrystallization from ethanol

Sources & evidence

ORD record
ord-f9d71f4aa9d44dc88da5818fd255ade2
Source dataset
uspto-grants-1981_03
Patent number
US04255181

Reaction notes

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