Hydrogen Bromide → 2-Bromo-6-nitrobenzothiazole

HRID 1174905Notes

Reaction equation

HRID 1174905 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.N([O-])=O.[Na+].[BrH:18]>O.[Cu]Br>[Br:18][C:2]1[S:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 227042-Amino-6-nitrobenzothiazoleHCID 23668193Sodium Nitrite

Product 1

HCID 116230402-Bromo-6-nitrobenzothiazoleYield 93%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 962WaterSolvent

Procedure

Suspend 2-amino-6-nitrobenzthiazole (20.0 g, 102 mmol) and copper (I) bromide (1.75 g, 12.2 mmol) in 18% HBr (aqueous) (200 mL) and water (180 mL). Slowly add sodium nitrite (61.0 g, 884 mmol). Continue to stir at room temperature for 30 min. Filter and dry on the filter flask overnight, to afford the title compound (24.6 g, 93%). 1H NMR (400 MHz, DMSO-d6): δ 9.19 (d, 1H, J=2.2 Hz), 8.36 (dd, 1H, J=9.0, 2.4 Hz), 8.20 (d, 1H, J=9.2 Hz).

Workup

  1. filtrationFilter
  2. customdry on the filter flask overnight

Sources & evidence

ORD record
ord-c507d2e94c714d2b8cffa0726849d0a0
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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