Phthalic Anhydride → HCID 58978663, compound

HRID 1945360Notes

Reaction equation

HRID 1945360 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, 1 eq, 0.146 mol) and phthalic anhydride (23.8 g, 1.1 eq, 0.161 mol) were placed in a reaction vessel, and dichloromethane (1 l) was added thereto. Aluminum chloride (29.2 g, 1.5 eq, 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 at 0° C., and the reaction solution was extracted with an excess of dichloromethane and several 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 at 0° C.
  4. extractionthe reaction solution was extracted with an excess of dichloromethane and several 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-5a795198f3ba419784df4fbd90202d85
Source dataset
uspto-grants-2013_03
Patent number
US08395144B2

Reaction notes

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