Sodium Carbonate → 2-Amino-7-bromo-6-fluorobenzothiazole

HRID 389582Notes

Reaction equation

HRID 389582 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.C([O-])(=O)C.[Na+].[Br:17]Br.C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[S:3][C:4]2[C:10]([Br:17])=[C:9]([F:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24408BromineHCID 3199542-Amino-6-fluorobenzothiazoleHCID 517045Sodium Acetate

Product 1

HCID 227204172-Amino-7-bromo-6-fluorobenzothiazoleYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 2-amino-6-fluorobenzothiazole (245 mg, 1.46 mmol) and sodium acetate (244 mg, 2.97 mmol) in acetic acid (1.60 mL) was added bromine (1.0 M in AcOH, 1.60 mL, 1.60 mmol) at RT. The mixture was stirred at RT for 1 h. The mixture was then treated with aqueous Na2CO3 until pH=7 and extracted with EtOAc (3×30 mL). The combined organic fractions were washed with water (2×20 mL) and brine (30 mL), dried over MgSO4, filtered, and concentrated. Purification by ISCO chromatography (0 to 30% EtOAc:heptane) afforded 357 mg of the impure title compound as a dark brown solid (357 mg). MS (ESI): 246.92, 248.93 [M+H]+; HPLC tR=1.25 min (TOF: polar—3 min).

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined organic fractions were washed with water (2×20 mL) and brine (30 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by ISCO chromatography (0 to 30% EtOAc:heptane)

Sources & evidence

ORD record
ord-e5c1f1bfadc744d2980183fae42de591
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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