3,4-Difluorobenzeneboronic acid → HCID 131722469, compound

HRID 321895Notes

Reaction equation

HRID 321895 reaction equation
C(C1C=CC(CCC2C=CC([C:18]3[CH:23]=[C:22]([F:24])[C:21](I)=[C:20]([F:26])[CH:19]=3)=C(F)C=2)=CC=1)CC.[F:28][C:29]1[CH:30]=[C:31]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([CH2:44][CH2:45][CH3:46])=[CH:40][CH:39]=2)[CH:32]=[CH:33][C:34]=1I.OB(O)[C:49]1[CH:54]=[CH:53][C:52]([F:55])=[C:51]([F:56])[CH:50]=1>>[F:28][C:29]1[CH:30]=[C:31]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([CH2:44][CH2:45][CH3:46])=[CH:40][CH:39]=2)[CH:32]=[CH:33][C:34]=1[C:20]1([F:26])[CH2:19][CH:18]=[CH:23][C:22]([F:24])=[C:21]1[C:49]1[CH:54]=[CH:53][C:52]([F:55])=[C:51]([F:56])[CH:50]=1

Participants

4

Reactant 3

HCID 27343373,4-Difluorobenzeneboronic acidHCID 18513409HCID 18513409, compoundHCID 22007974HCID 22007974, compound

Product 1

HCID 131722469HCID 131722469, compound

Procedure

The same procedures as in the fourth step were repeated with the exception that 4.3 g (8.9 mmol) of the 4′-(2-(4-propylphenyl)ethyl)-2′,3,5-trifluoro-4-iodobiphenyl obtained in the fifth step was used in place of the 3-fluoro-4-iodo-(2-(4-propylphenyl)ethyl)benzene used in the fourth step, and that 2.1 g (13.3 mmol) of dihydroxy(3,4-difluorophenyl)borane was used in place of dihydroxy(3,5-difluorophenyl)borane, to obtain 3.4 g of a crude 2″,2′,6′,3,4-pentafluoro-4″-(2-(4-propylphenyl)ethyl)terphenyl. This product was recrystallized from mixed solvent of ethanol/ethyl acetate (8/2) to obtain 2.6 g of the subject compound. (Yield: 62.3%) Phase transition temperatures of this product were as follows:

Workup

  1. customobtained in the fifth step

Sources & evidence

ORD record
ord-b2f12b4f404b49d39a0d9ee149f237b9
Source dataset
uspto-grants-2001_04
Patent number
US06210603B1

Reaction notes

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