Trifluoroacetic acid → Methyl 2-([2-(3-hydroxyphenyl)ethyl]thio}benzoate

HRID 2112037Notes

Reaction equation

HRID 2112037 reaction equation
C([O:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][S:14][C:15]2[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])[CH:9]=[CH:10][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][S:14][C:15]2[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68872701HCID 68872701, compound

Product 1

HCID 68873442Methyl 2-([2-(3-hydroxyphenyl)ethyl]thio}benzoateYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-{[2-(3-tert-butoxyphenyl)ethyl]thio}benzoate (402 mg, 1.167 mmol) was dissolved in DCM (3 ml). Trifluoroacetic acid (3 ml) was added. The mixture was stirred overnight and then evaporated to dryness. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using ethyl acetate/heptane (2.5:97.5, then 5:95, then 10:90 and then 25:75) as eluant gave 260 mg the desired product, yield 77%. 1H NMR (500 MHz, CDCl3): δ 2.94 (t, 2H), 3.17 (t, 2H), 3.95 (s, 3H), 6.18 (s, 1H) 6.77-6.83 (m, 3H), 7.18 (t, 2H), 7.34 (d, 1H), 7.44 (t, 1H) and 7.99 (d, 1H).

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-43ca14c87a9c40c0a5f910646d990d6d
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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