Potassium Carbonate → 4'-(6-Bromohexyloxy)biphenyl-4-carboxylic acid 2-methylbutyl ester

HRID 2073150Notes

Reaction equation

HRID 2073150 reaction equation
[CH3:1][CH:2]([CH2:20][CH3:21])[CH2:3][O:4][C:5]([C:7]1(O)[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH2:8]1)=[O:6].[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br.C(=O)([O-])[O-:31].[K+].[K+]>CC(C)=O>[CH3:1][CH:2]([CH2:20][CH3:21])[CH2:3][O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:31][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][Br:22])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 678606924-Hydroxybiphenyl-4-carboxylic acid 2-methylbutyl ester

Product 1

HCID 543845074'-(6-Bromohexyloxy)biphenyl-4-carboxylic acid 2-methylbutyl esterYield 60.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

70 mmols (19.9 g) of said ester 1a, 100 mmols (24.4 g) of 1,6-dibromohexane and 150 mmols (20.7 g) of potassium carbonate were refluxed in 400 ml of acetone for 8 hours. The reaction mixture was filtered and then purified by column chromatography to obtain 4'-(6-bromohexyloxy)biphenyl-4-carboxylic acid 2-methylbutyl ester (ether 5b; 18.9 g, yield 60%, [α]23D=+2.93 (chloroform)).

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-1977c7f3c6cb4eb09061377b4a944589
Source dataset
uspto-grants-1990_04
Patent number
US04915867

Reaction notes

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