N-bromobutanimide → 2-bromo-5,3'-dimethoxybiphenyl

HRID 1828403Notes

Reaction equation

HRID 1828403 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[Br:17]N1C(=O)CCC1=O>CN(C)C=O>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 802653,3'-Dimethoxy-1,1'-biphenyl2×

Product 1

HCID 115728962-bromo-5,3'-dimethoxybiphenylYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

3,3′-dimethoxybiphenyl (5.0 g, 23.34 mmol) was dissolved in a dimethylformamide solvent and cooled to 0° C. N-bromosuccinimide (4.15 g, 23.34 mmol) was dissolved in a dimethylformamide solvent (63 ml) and added slowly to a solution of 3,3′-dimethoxybiphenyl for about 1.5 hours. The mixture was stirred at room temperature for about 12 hours and distilled water was added thereto, followed by stirring for about 10 minutes. The resultant was filtered three times with hexane and the filtrate was washed three times with distilled water and dried over sodium sulfate. Hexane was removed under reduced pressure to obtain a desired product (Yield: 6.70 g, 98%). The obtained product was identified as 2-bromo-5,3′-dimethoxybiphenyl through the nuclear magnetic resonance (NMR) spectrum, corresponding to the compound I of the reaction scheme 2.

Workup

  1. distillationdistilled water
  2. additionwas added
  3. stirringby stirring for about 10 minutes
  4. filtrationThe resultant was filtered three times with hexane
  5. washthe filtrate was washed three times with distilled water
  6. dry with materialdried over sodium sulfate
  7. customHexane was removed under reduced pressure

Sources & evidence

ORD record
ord-5909df4700ee4c21a7afdd9c1511b8c7
Source dataset
uspto-grants-2006_06
Patent number
US07057074B2

Reaction notes

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