Dimethylformamide → HCID 67775982, compound

HRID 539261Notes

Reaction equation

HRID 539261 reaction equation
[CH3:1][O:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.CN(C)C=O.[Br:25]N1C(=O)CCC1=O>O>[Br:25][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 67184N-bromobutanimideHCID 67775933HCID 67775933, compound

Product 1

HCID 67775982HCID 67775982, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

13.4 g of 2-methoxy-3-(2-fluorophenyl)naphthalene and 100 mL of N,N-dimethylformamide were placed in a flask. Then, 40 mL of a N,N-dimethylformamide solution of 11.3 g of N-bromosuccinimide was added. The reaction solution was stirred at 60° C. for 8 hours. After cooling to room temperature, 500 mL of water was added. Then, an organic substance was extracted with toluene. The toluene solution was sequentially washed with sodium thiosulfate and saturated saline. After drying with magnesium sulfate, the organic phase was concentrated. Residues were purified by silica gel column chromatography, whereby 15.8 g (yield: 95%) of 1-bromo-2-methoxy-3-(2-fluorophenyl)naphthalene was obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThen, an organic substance was extracted with toluene
  3. washThe toluene solution was sequentially washed with sodium thiosulfate and saturated saline
  4. dry with materialAfter drying with magnesium sulfate
  5. concentrationthe organic phase was concentrated
  6. customResidues were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8a824980931e4783bf4baf7b56861ba9
Source dataset
uspto-grants-2014_10
Patent number
US08866135B2

Reaction notes

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