Boron tribromide → HCID 22312839, compound

HRID 965609Notes

Reaction equation

HRID 965609 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:18]=[CH:17][C:11]3[NH:12][C:13](=[O:16])[CH2:14][O:15][C:10]=3[CH:9]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:18]=[CH:17][C:11]3[NH:12][C:13](=[O:16])[CH2:14][O:15][C:10]=3[CH:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11369272HCID 11369272, compound

Product 1

HCID 22312839HCID 22312839, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(4-methoxyphenoxy)-2H-1,4-benzoxazin-3(4H)-one (120 mg; 0.44 mmol) in CH2Cl2 (1 ml) was treated with BBr3 (332 mg; 1.33 mmol). The mixture was stirred at room temperature for 3 hours. After evaporation to dryness the residue was taken up in EtOAc and water. The organic phase was washed with brine and dried over MgSO4. The residue (110 mg) was triturated with EtOAc, filtered and dried to give 7-(4-hydroxyphenoxy)-2H-1,4-benzoxazin-3(4H)-one as a biege solid (85 mg), Melting point 250-251° C.

Workup

  1. customAfter evaporation to dryness the residue
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. customThe residue (110 mg) was triturated with EtOAc
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-3e206261e7004635aa66b5d8b102812a
Source dataset
uspto-grants-2005_10
Patent number
US06951855B2

Reaction notes

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