Boron tribromide → HCID 22312857, compound

HRID 965610Notes

Reaction equation

HRID 965610 reaction equation
C[O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][S:8][C:9]2[CH:19]=[CH:18][C:12]3[NH:13][C:14](=[O:17])[CH2:15][O:16][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][S:8][C:9]2[CH:19]=[CH:18][C:12]3[NH:13][C:14](=[O:17])[CH2:15][O:16][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22312852HCID 22312852, compound

Product 1

HCID 22312857HCID 22312857, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(4-methoxy-benzylsulfanyl)-2H-1,4-benzoxazin-3(4H)-one(150 mg; 0.5 mmol) in CH2Cl2 (2 ml) was treated with BBr3 (350 mg; 1.5 mmol). The mixture was stirred at room temperature overnight. After evaporation to dryness the residue was taken up in EtOAc and water. The organic phase was washed with water, brine and dried over MgSO4. The residue was triturated with EtOAc, filtered and dried to give 7-(4-hydroxybenzylsulfanyl)-2-H-1,4-benzoxazin-3(4H)-one as a beige solid (149 mg), Melting point 207-209° C. Yield: 100% 1H NMR spectrum (DMSO d6): 4.07(s, 2H); 4.56 (s, 2H); 6.68 (m, 2H); 6.81 (d, 1H); 6.91 (m, 2H); 7.11 (d, 2H); 9.35 (s, 1H); 10.72 (s, 1H). LCMS-ESI: 288 [MH]+

Workup

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

Sources & evidence

ORD record
ord-8ed44b9df2764e0f949ec820234dd348
Source dataset
uspto-grants-2005_10
Patent number
US06951855B2

Reaction notes

Loading…