2-Isobutylthiazole → 5-Bromo-2-isobutyl-1,3-thiazole

HRID 2197573Notes

Reaction equation

HRID 2197573 reaction equation
[CH2:1]([C:5]1[S:6][CH:7]=[CH:8][N:9]=1)[CH:2]([CH3:4])[CH3:3].[Br:10]N1C(=O)CCC1=O.C(OCC)(=O)C.CCCCCC>CN(C=O)C>[Br:10][C:7]1[S:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[N:9][CH:8]=1

Participants

5

Reactant 3

HCID 627252-IsobutylthiazoleHCID 67184N-bromobutanimideHCID 21226206Ethyl acetate hexane

Product 1

HCID 206967745-Bromo-2-isobutyl-1,3-thiazoleYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-isobutylthiazole (600 mg, 4.25 mmol) in DMF (2 mL) was added N-bromosuccinimide (1.134 g, 6.37 mmol). The mixture was stirred at room temperature for 3 hours then subjected to flash column chromatography using 10% ethyl acetate/hexane to give a yellow oil (815.2 mg, 87% yield). LCMS (Conditions C): Tr 3.51 min; (M+H)': 219.90 (100%), 221.90 (100%).

Sources & evidence

ORD record
ord-c06ef94779544039aaed4cc7cded43bc
Source dataset
uspto-grants-2012_12
Patent number
US08338604B2

Reaction notes

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