N-bromobutanimide → HCID 71237985, compound

HRID 340066Notes

Reaction equation

HRID 340066 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([O:10][CH3:11])[CH:4]=1)[CH3:2].C1C(=O)N([Br:19])C(=O)C1>CC#N>[Br:19][C:8]1[CH:7]=[C:6]([F:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59789185HCID 59789185, compound

Product 1

HCID 71237985HCID 71237985, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 4-ethyl-1-fluoro-2-methoxy-benzene (WO 2010/090537, 12.2 g, 79.1 mmol) in MeCN (150 mL) was added a solution of NBS (14.4 g, 80.7 mmol) in MeCN (50 mL). The resulting solution was stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue was diluted with diethyl ether (150 mL). Precipitated solid was removed by filtration and the filtrate was washed with sodium sulfite aqueous solution (100 mL) and brine (100 mL), dried over MgSO4 and concentrated in vacuo to give the title compound as a yellow oil (18 g) in a 97% yield.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with diethyl ether (150 mL)
  3. customPrecipitated solid
  4. customwas removed by filtration
  5. washthe filtrate was washed with sodium sulfite aqueous solution (100 mL) and brine (100 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ead066270813402393b301a8d5deb296
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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