Acetic Acid → 2-[3-(4-Trifluoromethyl-benzyloxycarbonylmethyl)-phenylsulfanylmethyl]-benzoic acid

HRID 709506Notes

Reaction equation

HRID 709506 reaction equation
ClC(Cl)(Cl)C[O:4][C:5](=[O:35])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[O:22])[CH:15]=1.CC(O)=O>C(Cl)Cl.[Zn]>[F:34][C:31]([F:32])([F:33])[C:28]1[CH:29]=[CH:30][C:25]([CH2:24][O:23][C:21]([CH2:20][C:16]2[CH:15]=[C:14]([S:13][CH2:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[C:5]([OH:35])=[O:4])[CH:19]=[CH:18][CH:17]=2)=[O:22])=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 866503082-[3-(4-Trifluoromethyl-benzyloxycarbonylmethyl)-phenylsulfanylmethyl]-benzoic acid 2,2,2-trichloro-ethyl ester

Product 1

HCID 581194722-[3-(4-Trifluoromethyl-benzyloxycarbonylmethyl)-phenylsulfanylmethyl]-benzoic acidYield 70%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

2-[3-(4-Trifluoromethyl-benzyloxycarbonylmethyl)-phenylsulfanylmethyl]-benzoic acid 2,2,2-trichloro-ethyl ester (105 mg, 0.177 mmol) was dissolved in DCM (8 mL) and zinc (232 mg, 3.55 mmol) was added. After stirring for 5 minutes HOAc, 97% (1 mL, 18 mmol) was added dropwise. The resulting slurry was stirred for 1.5 h before zinc was filtered off and washed with DCM. The organic phase was washed with water, dried through a phase separator and concentrated. The crude was submitted to flash chromatography using heptane and EtOAc (70/30-60/40) as eluent to give the titled compound (57 mg, 70%) as an oil; 1H NMR (400 MHz, CDCl3): δ 3.64 (s, 2H), 4.56 (s, 2H), 5.18 (s, 2H), 7.09-7.14 (m, 1H), 7.16-7.21 (m, 2H), 7.22-7.34 (m, 3H), 7.36-7.43 (m, 3H), 7.60 (d, 2H), 8.00 (d, 1H); Mass spectrum: M−H+ 459.

Workup

  1. additionwas added dropwise
  2. filtrationwas filtered off
  3. washwashed with DCM
  4. washThe organic phase was washed with water
  5. customdried through a phase separator
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cfd3b63746004842833518998ff7abc0
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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