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Triethylamine → 4-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butyryl]-2-methyl-benzoic acid tert-butyl ester

HRID 1522774
Notes
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Reaction equation

HRID 1522774 reaction equation
[C:1]([O:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:28])/[CH:14]=[C:15](\[C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)/[C:16]([F:19])([F:18])[F:17])=[CH:9][C:8]=1[CH3:29])([CH3:4])([CH3:3])[CH3:2].C(O)(=[S:33])C.C(N(CC)CC)C>C(N(CC)CC)C.O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:28])[CH2:14][C:15]([C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)([SH:33])[C:16]([F:17])([F:19])[F:18])=[CH:9][C:8]=1[CH3:29])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 866959924-[(E)-3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-2-methyl-benzoic acid tert-butyl esterHCID 178418634HCID 178418634, compound

Product 1

HCID 894445754-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butyryl]-2-methyl-benzoic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 8471
Triethylamine
Catalyst
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To 4-[(E)-3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-2-methyl-benzoic acid tert-butyl ester (25 g) was added thioacetic acid (6 eq.) and triethylamine (200 μL) The solution was stirred at room temperature 2 drops of triethylamine were added. After stirring at room temperature for 24 hours, the mixture was poured in a mixture of water and ethyl acetate, extracted with ethyl acetate and washed with brine. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/dichloromethane) to give 4-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-mercapto-butyryl]-2-methyl-benzoic acid tert-butyl ester (3.78 g) 1H NMR (CDCl3, 400 MHz): δ=7.89 (d, J=8.8 Hz, 1 H), 7.72-7.79 (m, 2 H), 7.53-7.57 (m, 2 H), 7.35 (t, J=1.8 Hz, 1 H), 4.30 (d, J=18.3 Hz, 1 H), 3.97 (d, J=18.3 Hz, 1 H), 3.30 (s, 1 H), 2.59-2.65 (m, 3 H), 1.58-1.66 (m, 10 H), 1.56 ppm (s, 1 H).

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe collected organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated under vacuo
  7. customThe residue was purified by chromatography on silica gel (eluent: cyclohexane/dichloromethane)

Sources & evidence

ORD record
ord-cfa40482d6e14f9b85e096970a2bea3e
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09078444B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes