Triphenylphosphine → 4-[[2-Chloro-4-[(4-trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acid ethyl ester

HRID 985052Notes

Reaction equation

HRID 985052 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][C:15]=2[Cl:22])=[CH:9][C:8]=1[CH3:23])[CH3:2].O[C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[CH:16][C:15]=2[Cl:22])=[CH:9][C:8]=1[CH3:23])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 207681184-[(2-Chloro-4-hydroxymethylphenyl)sulfanyl]-2-methylphenoxy-acetic acid ethyl ester

Product 1

HCID 207681144-[[2-Chloro-4-[(4-trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An oven-dried 1 L round-bottomed flask was charged with compound 10.5 (33.5 g, 91.3 mmol), 4-hydroxybenzotrifluoride (16.3 g, 101 mmol), triphenylphosphine (28.7 g, 109 mmol) and THF (335 mL). Next, diethyl azodicarboxylate (17.0 mL, 110 mmol) was added dropwise at 0° C., and the reaction was stirred at room temperature for 30 min. The reaction mixture was concentrated and purified by flash chromatography (SiO2 gel 60 N, eluted with 10% AcOEt/hexanes—15% AcOEt/hexane—20% AcOEt/hexane). The fractions containing only desired product were combined and concentrated to a slightly yellow oil (43.4 g). 1H NMR (400 MHz) (CDCl3) δ 7.54 (2H, d, J=8.8 Hz); 7.42 (1H, d, J=1.6 Hz); 7.34-7.30 (2H, m); 7.09 (1H, dd, J=1.8, 8.2 Hz); 6.99 (2H, d, J=8.8 Hz); 6.76-6.72 (2H, m); 5.00 (2H, s); 4.68 (2H, s); 4.28 (2H, q, J=7.1 Hz); 2.29 (3H, s); 1.31 (3H, t, J=7.2 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash chromatography (SiO2 gel 60 N, eluted with 10% AcOEt/hexanes—15% AcOEt/hexane—20% AcOEt/hexane)
  3. additionThe fractions containing only desired product
  4. concentrationconcentrated to a slightly yellow oil (43.4 g)

Sources & evidence

ORD record
ord-1090ce84b12c42d5b45cb05d587e903b
Source dataset
uspto-grants-2005_03
Patent number
US06869975B2

Reaction notes

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