Dichloromethane → HCID 58978663, compound

HRID 517309Notes

Reaction equation

HRID 517309 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.ClCCl.[Cl-].[Al+3].[Cl-].[Cl-]>O>[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

6

Reactant 4

HCID 6344DichloromethaneHCID 6811Phthalic AnhydrideHCID 6451240Aluminum(III) ChlorideHCID 109456062-Bromo-9,9-dimethylfluorene

Product 1

HCID 58978663HCID 58978663, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-bromo-9,9-dimethyl-9H-fluorene (25.0 g, 0.092 mol) and phthalic anhydride (17.68 g, 0.119 mol) were placed in a reaction vessel, and added with dichloromethane (700 ml). At 0° C., aluminum chloride (18.5 g, 0.138 mol) was gradually added thereto, and the temperature was raised up to room temperature. Then, the resultant mixture was stirred for 12 hours. After the reaction was completed, the resultant product was gradually added with distilled water. The resultant product was extracted with an excess of dichloromethane, and washed several times with distilled water. After solvent removal, the produced solid was placed in a Hexane 2 l-containing vessel, washed, filtered, and dried, 2-(7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl)benzoic acid (23.2 g, yield 60%) was obtained.

Workup

  1. extractionThe resultant product was extracted with an excess of dichloromethane
  2. washwashed several times with distilled water
  3. customAfter solvent removal
  4. additioncontaining vessel
  5. washwashed
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-53164b54105d452ba2d970150e7c731d
Source dataset
uspto-grants-2015_08
Patent number
US09115112B2

Reaction notes

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