Dimethylformamide → 4-Bromo-1,2-bis[(2-ethylhexyl)oxy]benzene

HRID 217580Notes

Reaction equation

HRID 217580 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH2:9]([CH:11]([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])[CH3:10].CN(C=O)C>O>[Br:8][C:18]1[CH:17]=[CH:16][C:15]([O:20][CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])=[C:14]([O:13][CH2:12][CH:11]([CH2:9][CH3:10])[CH2:29][CH2:30][CH2:31][CH3:32])[CH:19]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimide2×HCID 14645488HCID 14645488, compound

Product 1

HCID 178485884-Bromo-1,2-bis[(2-ethylhexyl)oxy]benzeneYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Solid NBS (26.21 g, 0.147 mol) was added to an ice cold CH2Cl2 solution (250 mL) of 1b under N2 in the absence of light. Just enough DMF was added (30 mL) to disolve the NBS. The reaction mixture was allowed to warm to room temperature and then stirred for 12 h. The mixture was then poured into water. The organic layer was washed with a saturated LiCl solution and water. After drying with MgSO4 the solvent was removed under reduced pressure. The remaining oil was distilled (160° C./0.01 mmHg) to yield 4-bromo-1,2-di(2-ethylhexyloxy)benzene (2b) in 96% yield as a colorless oil.

Workup

  1. washThe organic layer was washed with a saturated LiCl solution and water
  2. dry with materialAfter drying with MgSO4 the solvent
  3. customwas removed under reduced pressure
  4. distillationThe remaining oil was distilled (160° C./0.01 mmHg)

Sources & evidence

ORD record
ord-3880cb73deb64f208199c98cb38e60b7
Source dataset
uspto-grants-2012_06
Patent number
US08198096B2

Reaction notes

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