Bromine → 6-Bromo-2-(methylthio)benzoxazole

HRID 1446878Notes

Reaction equation

HRID 1446878 reaction equation
[CH3:1][S:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[Br:12]Br>C(Cl)(Cl)Cl>[Br:12][C:10]1[CH:9]=[CH:8][C:6]2[N:7]=[C:3]([S:2][CH3:1])[O:4][C:5]=2[CH:11]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 41787732-(Methylthio)benzoxazole

Product 1

HCID 133148216-Bromo-2-(methylthio)benzoxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-(Methylthio)benzoxazole (5.8 g, see (a) above) was dissolved in chloroform (75 ml) and a solution of bromine (6.0 g) in chloroform (30 ml) was added dropwise, with stirring, over a period of 45 minutes. The mixture was allowed to stand overnight at room temperature and the solvent removed by distillation under reduced pressure to give a brown oil. The oil was washed with aqueous sodium metabisulfite and crystallised from ethanol/water to give the title compound as pink platelets (2.0 g), mp 95°-96° C.

Workup

  1. waitto stand overnight at room temperature
  2. customthe solvent removed by distillation under reduced pressure
  3. customto give a brown oil
  4. washThe oil was washed with aqueous sodium metabisulfite
  5. customcrystallised from ethanol/water

Sources & evidence

ORD record
ord-d45f6fc8ed7f4bca8a06934f7b836d9e
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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