4-Fluorophenol → HCID 86601034, compound

HRID 1180652Notes

Reaction equation

HRID 1180652 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14][S:15][CH3:16])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[F:17][C:18]1[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=1.C(N=C=NC(C)C)(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:7][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14][S:15][CH3:16])([CH3:1])[CH2:3][C:4]([O:6][C:21]1[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=1)=[O:5]

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 12734DiisopropylcarbodiimideHCID 86601035HCID 86601035, compound

Product 1

HCID 86601034HCID 86601034, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-methyl-3-(2-methyldisulfanylphenyl)butanoic acid, 4-fluorophenol (1.1 eq) and 4-(N,N-dimethylamino)pyridine (0.5 eq) in CH2Cl2 was added diisopropylcarbodiimide (1.5-2.0 eq) at 0° C. The mixture was stirred overnight at ambient temperature. The precipitate was filtered off and the filtrate concentrated by rotary evaporation. The crude product was purified on a silica gel column to afford 4-fluorophenyl 3-methyl-3-(2-methyldisulfanylphenyl)butanoate as a colorless oil in 62% yield: 1H NMR (CDCl3, 300 MHz) δ (ppm): 1.76 (s, 6H), 2.52 (s, 3H), 3.44 (s, 2H), 6.70 (dd, J=9.0, 4.2 Hz, 2H), 7.00 (t, J=9.0 Hz, 2H), 7.2-7.3 (m, 2H), 7.36 (dd, J=7.8, 1.5 Hz, 1H), 7.96 (dd, J=7.8, 1.2 Hz, 1H). 19F NMR (CD3CN, 282 MHz) δ (ppm): −119.2.

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate concentrated by rotary evaporation
  3. customThe crude product was purified on a silica gel column

Sources & evidence

ORD record
ord-cdcc1b1421644e5b98e148174bdf64ba
Source dataset
uspto-grants-2007_10
Patent number
US07282590B2

Reaction notes

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