Bromine → HCID 178419523, compound

HRID 1262664Notes

Reaction equation

HRID 1262664 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7](=[O:9])[CH3:8])[N:6]=1.[Br:10]Br>Br>[BrH:10].[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7](=[O:9])[CH2:8][Br:10])[N:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 178467223HCID 178467223, compound

Product 1

HCID 178419523HCID 178419523, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent2×

Procedure

2.40 g (19.3 mmol) of 1-(2-methyl-4-imidazolyl) ethanone was dissolved in 30 ml of 48% hydrogen bromide. To the stirred solution at 25° was added over a 5 minute period 3.36 g (21 mmol) of bromine dissolved in 5 ml 48% hydrogen bromide. The reaction was heated to 70° for 2.5 hours and then concentrated in vacuo to a dark oil. A mixture of isopropyl alcohol/ether was added and trituration of the oil gave a solid. This was collected by filtration and washed with ether to give 2.8 g (51%) of 1-(2-methyl-4-imidazolyl)-2-bromoethanone hydrobromide, mp 181° (dec.); nmr (DMSO-d6) (δ): 8.71 (s, 1H); 4.77 (s, 2H); 2.63 (s, 3H).

Workup

  1. temperatureThe reaction was heated to 70° for 2.5 hours
  2. concentrationconcentrated in vacuo to a dark oil
  3. additionA mixture of isopropyl alcohol/ether
  4. additionwas added
  5. customtrituration of the oil gave a solid
  6. filtrationThis was collected by filtration
  7. washwashed with ether

Sources & evidence

ORD record
ord-0dbbd0c6485e44109a61f8b2e7722ed5
Source dataset
uspto-grants-1984_06
Patent number
US04452987

Reaction notes

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