Sodium Iodide → Ethyl 4-(3-bromophenoxy)butanoate

HRID 707786Notes

Reaction equation

HRID 707786 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+].[CH2:17]([O:19][C:20](=[O:25])[CH2:21][CH2:22][CH2:23]Br)[CH3:18]>CC(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:23][CH2:22][CH2:21][C:20]([O:19][CH2:17][CH3:18])=[O:25]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 22407915Ethyl 4-(3-bromophenoxy)butanoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Solid 3-bromophenol (10.0 g, 58 mmol) was added portion wise to a stirred suspension of K2CO3 in acetone (100 mL) at room temperature. Sodium iodide (NaI, 1.0 g) was added, followed by ethyl-4-bromobutyrate (9.2 mL, 64 mmol). The reaction mixture was heated at 80° C. overnight, cooled to room temperature, diluted with water and extracted with ethylacetate to give ethyl 4-(3-bromophenoxyl)butanoate.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethylacetate

Sources & evidence

ORD record
ord-d2f6954f1b42459c87f5cdfc992b1211
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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