Dichlorodiphenylmethane → 4-Bromo-7-methoxy-2,2-diphenyl-1,3-benzodioxole

HRID 1057942Notes

Reaction equation

HRID 1057942 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:4]([OH:5])[C:3]=1[OH:11].[C:12]1([C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(Cl)Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>>[Br:1][C:2]1[C:3]2[O:11][C:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:5][C:4]=2[C:6]([O:9][CH3:10])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 16327DichlorodiphenylmethaneHCID 516892Sodium BicarbonateHCID 37058743-Bromo-6-methoxybenzene-1,2-diol

Product 1

HCID 227343704-Bromo-7-methoxy-2,2-diphenyl-1,3-benzodioxole

Procedure

3-Bromo-6-methoxycatechol (3.87 g) and diphenyl-dichloromethane (4.61 g) were heated at 170° C. with stirring without a solvent. After being allowed to stand for cooling, a saturated aqueous solution of sodium bicarbonate was added to the mixture, followed by extraction with ether. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was triturated with methanol to give Compound IIbl-a (4.7 g, 69%) as a white solid.

Workup

  1. temperaturefor cooling
  2. extractionfollowed by extraction with ether
  3. washThe organic layer was washed with a saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was triturated with methanol
  7. customto give Compound IIbl-a (4.7 g, 69%) as a white solid

Sources & evidence

ORD record
ord-ac30183301554d74a7b28e5047a25b67
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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