Aluminum(III) Chloride → 6-Bromo-5-hydroxy-2h-3,1-benzoxazine-2,4(1h)-dione

HRID 1725960Notes

Reaction equation

HRID 1725960 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7](=[O:12])[C:6]=2[C:13]=1[O:14]C.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7](=[O:12])[C:6]=2[C:13]=1[OH:14]

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 876056556-Bromo-5-methoxy-2h-3,1-benzoxazine-2,4(1h)-dione

Product 1

HCID 876051196-Bromo-5-hydroxy-2h-3,1-benzoxazine-2,4(1h)-dioneYield 94.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of Example 385B (20 g) in dichloromethane (600 mL) at 0° C. was treated with AlCl3 (39 g, 293 mmol) in several portions and stirred vigorously overnight at room temperature. The mixture was treated with brine (300 mL), stirred for 10 minutes, and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated to provide the desired product (18 g) which was used directly in the next step.

Workup

  1. stirringstirred for 10 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6ba792a99c6c431b971cda84939500c1
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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