Water → 2-Bromo-5-methoxybenzothiazole

HRID 1915618Notes

Reaction equation

HRID 1915618 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[S:12][C:11](S)=[N:10][C:9]=2[CH:14]=1.O>C(Cl)(Cl)Cl.CCOCC>[Br:1][C:11]1[S:12][C:8]2[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:14][C:9]=2[N:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 178488276HCID 178488276, compound

Product 1

HCID 220405252-Bromo-5-methoxybenzothiazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of bromine (3.6 eq) in chloroform (0.75M) was added dropwise over a period of 1 hr to a stirred suspension of 5-methoxy-2-mercaptobenzothiazole (1 eq) in chloroform at 0° C. The mixture was stirred for 30 min before it was added slowly to water and stirred for further 20 min. The mixture was filtered to remove a cream solid. The organic phase was dried and evaporated to leave a brown solid. The brown solid was dissolved in ether and filtered. The residue was washed with ether and the filtrate and washings were combined and evaporated, chromatographed (4:1 hexanes and ethyl acetate) to give the title compound as a pale yellow solid. MS: MH+=244

Workup

  1. stirringstirred for further 20 min
  2. filtrationThe mixture was filtered
  3. customto remove a cream solid
  4. customThe organic phase was dried
  5. customevaporated
  6. customto leave a brown solid
  7. filtrationfiltered
  8. washThe residue was washed with ether
  9. customevaporated
  10. customchromatographed (4:1 hexanes and ethyl acetate)

Sources & evidence

ORD record
ord-6026c35aa5b54c2380833e30c71e576d
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Reaction notes

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