Acetic Acid → 6-Bromo-2-(methylsulfanyl)-1,3-benzothiazole

HRID 1972981Notes

Reaction equation

HRID 1972981 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[Br:12]Br.C(O)(=O)C>C(Cl)(Cl)Cl>[Br:12][C:10]1[CH:9]=[CH:8][C:6]2[N:7]=[C:3]([S:2][CH3:1])[S:4][C:5]=2[CH:11]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 119892-(Methylthio)benzothiazoleHCID 24408Bromine

Product 1

HCID 179535146-Bromo-2-(methylsulfanyl)-1,3-benzothiazoleYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To the solution of 2-(methylthio)-1,3-benzothiazole (5.00 g, 27.58 mmol) in CHCl3 (85 mL) in a NaCl-ice water bath, bromine (4.24 mL, 82.8 mmol) was slowly added dropwise, followed by acetic acid (30 mL). The mixture was stirred at rt overnight. The white solid was filtered and then dissolved in EtOAc (200 mL). Saturated, aqueous Na2CO3 (200 mL) was added and the organic layer was separated, dried over MgSO4 and concentrated to dryness. Desired product (5.0 g, 70%) was obtained. 1H NMR (400 MHz, DMSO-d6) δ8.30 (s, 1H), 7.76 (d, 1H), 7.59 (d, 1H), 2.79 (s, 3H); LC-MS m/z [M+H]+ 260.2 & 262.1, RT 3.65 min.

Workup

  1. filtrationThe white solid was filtered
  2. dissolutiondissolved in EtOAc (200 mL)
  3. additionSaturated, aqueous Na2CO3 (200 mL) was added
  4. customthe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-200d274521f84ca79180dafde444de89
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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