Phthalic Anhydride → HCID 58978663, compound

HRID 40403Notes

Reaction equation

HRID 40403 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH3:16])([CH3:15])[C:4]=2[CH:3]=1.[C:17]1(=[O:27])[O:22][C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:12]([C:11]3[CH:10]=[CH:9][C:8]([C:17]([C:18]4[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=4[C:20]([OH:22])=[O:21])=[O:27])=[CH:7][C:6]=3[C:5]2([CH3:16])[CH3:15])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 6451240Aluminum(III) ChlorideHCID 109456062-Bromo-9,9-dimethylfluorene

Product 1

HCID 58978663HCID 58978663, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-bromo-9,9-dimethyl-9H-fluorene (40 g, 0.146 mol) and phthalic anhydride (23.8 g, 0.161 mol) were placed in a reaction vessel and dichloromethane (1 l) was added thereto. Then, aluminum chloride (29.2 g, 0.219 mol) was gradually added at 0° C., and the reaction mixture was stirred at room temperature for 12 hours. After the reaction was terminated, distilled water was gradually added, and the reaction solution was extracted with dichloromethane and 3 times washed with distilled water. After solvent removal, the resultant solid was placed in a hexane(2 l)-containing vessel, washed, filtered and dried to give 2-(7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl)benzoic acid (50.4 g, yield 82%).

Workup

  1. customAfter the reaction was terminated
  2. distillationdistilled water
  3. additionwas gradually added
  4. extractionthe reaction solution was extracted with dichloromethane and 3 times
  5. washwashed with distilled water
  6. customAfter solvent removal
  7. addition)-containing vessel
  8. washwashed
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-3bb0d38912764b8badcae15269f3cc36
Source dataset
uspto-grants-2013_09
Patent number
US08525158B2

Reaction notes

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