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Hydrogen Bromide → Butyl 2-bromo-3-[4-(2,4,5-trimethyl-3,6-dimethoxyphenoxy)phenyl]propionate

HRID 1742484
Notes
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Reaction equation

HRID 1742484 reaction equation
[BrH:1].N([O-])=O.[Na+].[CH3:6][O:7][C:8]1[C:21]([CH3:22])=[C:20]([CH3:23])[C:19]([O:24][CH3:25])=[C:18]([CH3:26])[C:9]=1[O:10][C:11]1[CH:17]=[CH:16][C:14](N)=[CH:13][CH:12]=1.[C:27]([O:31][CH2:32][CH2:33][CH2:34][CH3:35])(=[O:30])[CH:28]=[CH2:29]>O.CC(C)=O>[Br:1][CH:28]([CH2:29][C:14]1[CH:16]=[CH:17][C:11]([O:10][C:9]2[C:8]([O:7][CH3:6])=[C:21]([CH3:22])[C:20]([CH3:23])=[C:19]([O:24][CH3:25])[C:18]=2[CH3:26])=[CH:12][CH:13]=1)[C:27]([O:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 8846Butyl AcrylateHCID 190092414-(2,5-Dimethoxy-3,4,6-trimethylphenoxy)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 19009256Butyl 2-bromo-3-[4-(2,4,5-trimethyl-3,6-dimethoxyphenoxy)phenyl]propionate

Reagents, catalysts & solvents 2

HCID 180
Acetone
Solvent
HCID 962WaterSolvent2×

Procedure

7.7 g of a 47% w/v aqueous solution of hydrobromic acid and a solution of 1.3 g of sodium nitrite in 3 ml of water were added dropwise, in that order, to a solution of 4.3 g of 4-(2,5-dimethoxy-3,4,6-trimethylphenoxy)aniline [prepared as described in step (c) above] in 10 ml of acetone, after which 21 ml of butyl acrylate were added to the mixture. After that, 0.3 g of cupric bromide was gradually added and the resulting mixture was stirred at room temperature for 4 hours. At the end of this time, the reaction mixture was poured into water, after which it was extracted with benzene. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure from the extract, and the residue thus obtained was purified by column chromatography through silica gel, using a 3:7 by volume mixture of hexane and benzene as the eluent, to give 5.7 g of the title compound.

Workup

  1. extractionafter which it was extracted with benzene
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure from the extract
  5. customthe residue thus obtained
  6. customwas purified by column chromatography through silica gel
  7. additionby volume mixture of hexane and benzene as the eluent

Sources & evidence

ORD record
ord-1fab982774ff4304b0552720d46d69d2
Source dataset
uspto-grants-1994_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05338855

Reaction notes

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