Acetonitrile → 1-Bromo-4-methoxy-2-methylbenzene

HRID 716459Notes

Reaction equation

HRID 716459 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[CH:4]=1.C(#N)C.C1C(=O)N([Br:20])C(=O)C1>>[Br:20][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH3:9]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 75303-MethoxytolueneHCID 67184N-bromobutanimide

Product 1

HCID 1179151-Bromo-4-methoxy-2-methylbenzeneYield 86%

Conditions

Temperature
10 °C

Procedure

To a solution of 122 g (1.0 mol) of 1-methoxy-3-methylbenzene in 1 L of acetonitrile 178 g (1.0 mol) of NBS was added in small portions by vigorous stirring for 1 h at 10° C. The reaction mixture was stirred at ambient temperature overnight and then evaporated to dryness. The residue was dissolved in 1 L of n-hexane and filtered through glass frit (G2). The precipitate was additionally washed by 2×150 ml of n-hexane. The combined filtrate was evaporated to dryness to give 173 g (86%) of 1-bromo-4-methoxy-2-methylbenzene.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature overnight
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in 1 L of n-hexane
  4. filtrationfiltered through glass frit (G2)
  5. washThe precipitate was additionally washed by 2×150 ml of n-hexane
  6. customThe combined filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-47b6525a07c542d48306fdb333932ac7
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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