Tert-Butyl nitrite → 7-Bromo-6-fluorobenzothiazole

HRID 389583Notes

Reaction equation

HRID 389583 reaction equation
N[C:2]1[S:3][C:4]2[C:10]([Br:11])=[C:9]([F:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.N(OC(C)(C)C)=O>C1COCC1>[Br:11][C:10]1[C:4]2[S:3][CH:2]=[N:6][C:5]=2[CH:7]=[CH:8][C:9]=1[F:12]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 227204172-Amino-7-bromo-6-fluorobenzothiazole

Product 1

HCID 667604487-Bromo-6-fluorobenzothiazoleYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of impure 2-amino-7-bromo-6-fluorobenzothiazole from Step A in THF (10 mL) was added tert-butyl nitrite (90%, 1.25 mL, 9.46 mmol). The mixture was stirred at 50° C. for 7 h and then purified by ISCO chromatography (0 to 40% EtOAc:heptane) to afford 114 mg (34%) of the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.54 (dd, J=2.4, 8.0 Hz, 1H), 7.62 (dd, J=2.4, 8.0 Hz, 1H), 9.03 (s, 1H); 19F NMR (376 MHz, CDCl3): δ−113.77; MS (ESI): 231.92/233.92 [M+H]+; HPLC tR=1.38 min (TOF: polar—3 min).

Workup

  1. custompurified by ISCO chromatography (0 to 40% EtOAc:heptane)

Sources & evidence

ORD record
ord-2b3a2480f3684563a76edd4142990b41
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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