2(3H)-Benzoxazolone → 6-Bromo-2(3H)-benzoxazolone

HRID 1864797Notes

Reaction equation

HRID 1864797 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].[Br:11]Br>C(Cl)Cl>[Br:11][C:7]1[CH:8]=[CH:9][C:4]2[NH:3][C:2](=[O:10])[O:1][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 60432(3H)-BenzoxazoloneHCID 24408Bromine

Product 1

HCID 298596-Bromo-2(3H)-benzoxazolone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3H-benzooxazol-2-one (20 g, 0.15 mol) in DCM (500 mL) was added bromine (8.34 mL, 0.16 mol). After stifling at room temperature for 19.5 h, the orange precipitate that had formed was filtered off and washed with DCM until the orange color was washed out. The filtrate was concentrated to approximately 33% of its original volume and filtered and washed as before. The combined solids weighed 28.36 g and contained ca. 8-9% starting material.

Workup

  1. customthe orange precipitate that had formed
  2. filtrationwas filtered off
  3. washwashed with DCM until the orange color
  4. washwas washed out
  5. concentrationThe filtrate was concentrated to approximately 33% of its original volume
  6. filtrationfiltered
  7. washwashed as before

Sources & evidence

ORD record
ord-ba7a4482011846cba8cedf02f163aa73
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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