Dichloromethane → HCID 67536104, compound

HRID 517307Notes

Reaction equation

HRID 517307 reaction equation
[CH3:1][C:2]1([CH3:15])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[Br:16][C:17]1[CH:18]=[C:19]2[C:24](=[O:25])[O:23][C:21](=[O:22])[C:20]2=[CH:26][CH:27]=1.ClCCl.[Cl-].[Al+3].[Cl-].[Cl-]>O>[Br:16][C:17]1[CH:27]=[CH:26][C:20]([C:21]([C:5]2[CH:6]=[CH:7][C:8]3[C:9]4[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:2]([CH3:15])([CH3:1])[C:3]=3[CH:4]=2)=[O:22])=[C:19]([CH:18]=1)[C:24]([OH:25])=[O:23]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 665904-Bromophthalic anhydrideHCID 783259,9-DimethylfluoreneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 67536104HCID 67536104, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9,9-dimethyl-9H-fluorene (27.78 g, 0.143 mol) and 4-Bromo Phthalic anhydride (48.69 g, 0.214 mol) were placed in a reaction vessel, and added with Dichloromethane (700 ml). At 0° C., aluminum chloride (28.7 g, 0.214 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, 5-bromo-2-(9,9-dimethyl-9H-fluorene-2-carbonyl)benzoic acid (30 g, yield 50%) 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-31148427d1894aea9026318c1e0f4e0f
Source dataset
uspto-grants-2015_08
Patent number
US09115112B2

Reaction notes

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