Triethylamine → 2-(5-(4-Fluorophenoxy)-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

HRID 226504Notes

Reaction equation

HRID 226504 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:33])[CH:12]([C:16]1[CH:17]=[C:18]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[CH:19]=[C:20]([OH:22])[CH:21]=1)[CH2:13][CH2:14][CH3:15])[CH3:9].[F:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1>CC([O-])=O.CC([O-])=O.[Cu+2].C(Cl)Cl>[CH2:8]([O:10][C:11](=[O:33])[CH:12]([C:16]1[CH:17]=[C:18]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:32])[F:31])=[CH:27][CH:28]=2)[CH:19]=[C:20]([O:22][C:38]2[CH:39]=[CH:40][C:35]([F:34])=[CH:36][CH:37]=2)[CH:21]=1)[CH2:13][CH2:14][CH3:15])[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2856454-Fluorophenylboronic acidHCID 24771789Ethyl 2-[5-hydroxy-4'-(trifluoromethyl)biphenyl-3-yl]pentanoate

Product 1

HCID 251117452-(5-(4-Fluorophenoxy)-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl esterYield 58.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (100 μL, 0.72 mmol) was added to a stirred mixture of 2-(5-hydroxy-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (90 mg, 0.25 mmol), Cu(OAc)2 (68 mg, 0.38 mmol), 4-fluorophenylboronic acid (70 mg, 0.57 mmol), 4 {acute over (Å)} molecular sieves (25 mg, powdered) and DCM (2 mL) at room temperature open to the air. After 24 h, the reaction mixture was loaded onto silica and purified (0-10% ethyl acetate in petrol) to give 2-(5-(4-fluorophenoxy)-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (67 mg) as a colourless oil.

Workup

  1. customat room temperature
  2. custompurified (0-10% ethyl acetate in petrol)

Sources & evidence

ORD record
ord-24b2a2ef31ad44e788d2117e447b65b6
Source dataset
uspto-grants-2009_07
Patent number
US07557244B2

Reaction notes

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