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

HRID 1435559Notes

Reaction equation

HRID 1435559 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 stirring 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. 1H NMR indicated the product was clean albeit contained ca. 8-9% starting material meaning the true yield of product was 26.72 g, 84%.

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-95260d047c5f41c3845a852f296af0ea
Source dataset
uspto-grants-2009_11
Patent number
US07618650B2

Reaction notes

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