Dimethylformamide → HCID 68585664, compound

HRID 18451Notes

Reaction equation

HRID 18451 reaction equation
CO[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:4]=1.[Br:18]N1C(=O)CCC1=O.CN([CH:29]=[O:30])C>>[Br:18][CH:9]([C:5]1[CH:4]=[CH:3][CH:8]=[CH:7][CH:6]=1)[CH:10]([O:30][CH3:29])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 200388771-Methoxy-3-nonyl benzene

Product 1

HCID 68585664HCID 68585664, compound

Procedure

A solution of 1-methoxy-3-nonyl benzene (7.5 g; 32 mmol) in DMF (60 mL) was cooled to −10° C. and N-bromosuccinimide (5.42 g; 30 mmol) was added under stirring over 30 minutes. The MeOH/ice bath was removed after 1 hour and the reaction mixture was left overnight with stirring. The reaction mixture was poured onto H2O (100 mL) and 10 M NaOH (aq) was added. The alkaline slurry was extracted with EtOAc (2×) and the combined organic fractions washed with 1 M NaOH (aq.; 2×), dried (MgSO4), filtered and evaporated to dryness. The crude product was further purified by column chromatography (SiO2; EtOAc/PE80-100° C.=0:1→1:20) to yield 9.8 g (quantitative) of product with satisfactory purity.

Workup

  1. customThe MeOH/ice bath was removed after 1 hour
  2. waitthe reaction mixture was left overnight
  3. stirringwith stirring
  4. additionThe reaction mixture was poured onto H2O (100 mL) and 10 M NaOH (aq)
  5. additionwas added
  6. extractionThe alkaline slurry was extracted with EtOAc (2×)
  7. washthe combined organic fractions washed with 1 M NaOH (aq.; 2×)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe crude product was further purified by column chromatography (SiO2; EtOAc/PE80-100° C.=0:1→1:20)
  12. customto yield 9.8 g (quantitative) of product with satisfactory purity

Sources & evidence

ORD record
ord-0922995d2f0247e2a66c89c5cf865627
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Reaction notes

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