Dichlorodiphenylmethane → 5-Bromo-6-fluoro-2,2-diphenyl-2H-1,3-benzodioxole

HRID 1352210Notes

Reaction equation

HRID 1352210 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5]([OH:9])=[CH:6][C:7]=1[F:8].[C:11]1([C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(Cl)Cl)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CO>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]2[O:9][C:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 16327DichlorodiphenylmethaneHCID 218653784-Bromo-5-fluorobenzene-1,2-diol

Product 1

HCID 218653865-Bromo-6-fluoro-2,2-diphenyl-2H-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-bromo-5-fluoro-benzene-1,2-diol (12 g, 58.0 mmol) and diphenyldichloromethane (1.2 eq., 16.50 g) was stirred at room temperature until gaseous evolution ceased. The mixture was heated with stirring at 180° C. for 20 min. The reaction mixture was allowed to cool to room temperature, diluted with methanol (50 ml) and vigorously stirred. The precipitated product was collected by filtration and dissolved in toluene (50 ml). Methanol (100 ml) was added and the mixture stirred 30 min at room temperature. The precipitated product was collected by filtration (yield 10.3 g, 48%), a further batch (6.4 g, 30%) was recovered from the mother liquors.

Workup

  1. temperatureThe mixture was heated
  2. stirringwith stirring at 180° C. for 20 min
  3. temperatureto cool to room temperature
  4. stirringvigorously stirred
  5. filtrationThe precipitated product was collected by filtration
  6. dissolutiondissolved in toluene (50 ml)
  7. additionMethanol (100 ml) was added
  8. stirringthe mixture stirred 30 min at room temperature
  9. filtrationThe precipitated product was collected by filtration (yield 10.3 g, 48%)
  10. customa further batch (6.4 g, 30%) was recovered from the mother liquors

Sources & evidence

ORD record
ord-34bd1532b41b4ad7b83285614a7f8c05
Source dataset
uspto-grants-2007_05
Patent number
US07220743B2

Reaction notes

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