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4-Hydroxybenzaldehyde → 4-[2-Bromo-2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde

HRID 1922047
Notes
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Reaction equation

HRID 1922047 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[Br:12][CH:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][N:17]=1)[CH2:14]Br>CN(C=O)C>[Br:12][CH:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][N:17]=1)[CH2:14][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 143917832-(1,2-Dibromoethyl)-5-ethylpyridine

Product 1

HCID 713792484-[2-Bromo-2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of 0.67 g (0.0055 mol) p-hydroxy benzaldehyde and 0.237 g (0.0098 mol) sodium hydride in 10 mL DMF, 1 g (0.0034 mol) 2-bromo-[5-ethyl-2-pyridyl]-ethyl bromide dissolved in 10 mL of DMF was added at 10-15° C. Reaction mixture was stirred for 1 hr at 25-30° C. and further warmed at 75-80° C. for 24 hr. After subsequent work-up crude product was obtained which on purification gave titled compound. Yield of the product was 0.068 g (6%). The product obtained was characterized by satisfactory mass.

Workup

  1. additionwas added at 10-15° C
  2. customReaction mixture
  3. temperaturefurther warmed at 75-80° C. for 24 hr
  4. customAfter subsequent work-up crude product was obtained which
  5. customon purification

Sources & evidence

ORD record
ord-6e71b8ed93d841deb3ef6374353e1e46
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173816B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes