Dimethylformamide → HCID 117992149, compound

HRID 531123Notes

Reaction equation

HRID 531123 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.[Br:14][C:15]1[C:27]([OH:28])=[CH:26][C:18]2[O:19][C:20]([CH3:25])([CH3:24])[O:21][C:22](=[O:23])[C:17]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:1]([O:28][C:27]1[C:15]([Br:14])=[CH:16][C:17]2[C:22](=[O:23])[O:21][C:20]([CH3:24])([CH3:25])[O:19][C:18]=2[CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 113916436-Bromo-7-hydroxy-2,2-dimethyl-benzo[1,3]dioxin-4-one

Product 1

HCID 117992149HCID 117992149, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzyl bromide (4.88 mL) was added to a DMF (50 mL) suspension of 6-bromo-7-hydroxy-2,2-dimethyl-4H-1,3-benzodioxin-4-one (9.34 g) and potassium carbonate (7.09 g), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was allowed to cool to room temperature, and then, water was added thereto, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained solid was washed with diethyl ether to obtain the title compound (9.95 g).

Workup

  1. temperatureto cool to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe obtained organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. washThe obtained solid was washed with diethyl ether

Sources & evidence

ORD record
ord-817a108c3b504a9cb01380fc364bb7b6
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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