Potassium Carbonate → 4'-(10-Bromodecyloxy)biphenyl-4-carboxylic acid ethyl ester

HRID 2072653Notes

Reaction equation

HRID 2072653 reaction equation
[CH2:1]([O:3][C:4]([C:6]1(O)[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH2:7]1)=[O:5])[CH3:2].[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br.C(=O)([O-])[O-:32].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:32][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][Br:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2214831,10-DibromodecaneHCID 68717694HCID 68717694, compound

Product 1

HCID 539849124'-(10-Bromodecyloxy)biphenyl-4-carboxylic acid ethyl esterYield 72.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

An acetone solution of 90 m moles (21.8 g) of 4-hydroxybiphenyl-4-carboxylic acid ethyl ester obtained in Example 24, 0.15 mole (45.0 g) of 1,10-dibromodecane, and 0.4 mole (55.3 g) of potassium carbonate was refluxed for four hours. The reaction solution was filtered. The filtrate was concentrated, and then purified by column chromatography, to obtain 29.9 g of 4'-(10-bromodecyloxy)biphenyl-4-carboxylic acid ethyl ester. (yield: 72%)

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-43e903540d754b398c05223e9b21838a
Source dataset
uspto-grants-1990_04
Patent number
US04913839

Reaction notes

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