Sodium Carbonate → 2',3'-Difluoro-4'-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid ethyl ester

HRID 6598

Reaction equation

HRID 6598 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:5]=[CH:4][C:3]=1B(O)O.[CH2:23]([O:30][C:31]1[CH:39]=CC(C(O)=O)=CC=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-:41].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1>[CH2:31]([O:30][C:23]([C:24]1[CH:29]=[CH:28][C:27]([C:3]2[CH:4]=[CH:5][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:7]([F:8])[C:2]=2[F:1])=[CH:26][CH:25]=1)=[O:41])[CH3:39]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 738804-(Benzyloxy)benzoic acidHCID 220162552,3-Difluoro4-(4-pentyloxybutoxy)phenylboronic acid

Product 1

HCID 235428492',3'-Difluoro-4'-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid ethyl esterYield 88%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 22272177Toluene waterSolvent

Procedure

A biphasic solution of 2,3-difluoro-4-(4-pentyloxybutoxy)phenylboronic acid (25) (1 equi.), 4-bromo-benzoic acid ethyl ester (12), (1 equi.), sodium carbonate (2.7 equi.), and tetrakis(triphenylphoshine)palladium catalyst (0.01 equi.) in water-toluene (1:1) (2 mL/mmole) was stirred at 100 C. temperature for 12 h., cooled to room temperature, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. The purification by chromatography on silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile afforded 2′,3′-difluoro-4′-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid ethyl ester (26) as a white solid (88%).

Workup

  1. extractionextracted with ethyl acetate:hexane(1:1)
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe purification by chromatography
  6. customon silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-6ad8b409962b46c38cd36eb904e5406a
Source dataset
uspto-grants-2006_08
Patent number
US07083832B2

Linked notes

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