Dimethylformamide → 1-Bromo-2-methoxy-3-(2-fluorophenyl)naphthalene

HRID 470732Notes

Reaction equation

HRID 470732 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 677759821-Bromo-2-methoxy-3-(2-fluorophenyl)naphthaleneYield 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-53b1aa50a05c4245af3cb2ebd6352ee5
Source dataset
uspto-grants-2014_01
Patent number
US08629430B2

Reaction notes

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