1-Octanethiol → Ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoate

HRID 2110848Notes

Reaction equation

HRID 2110848 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[Cl-].[Al+3].[Cl-].[Cl-].C(S)CCCCCCC>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 81441-OctanethiolHCID 6451240Aluminum(III) ChlorideHCID 23083097Ethyl 3-(2-Fluoro-4-methoxyphenyl)propanoate

Product 1

HCID 23082888Ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-(2-fluoro-4-methoxyphenyl)propanoate (57.4 g, 254 mmol) and aluminum chloride (101 g, 761 mmol) in dichloromethane (250 mL) was added dropwise 1-octanethiol (74.3 g, 508 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into ice water, and the mixture was stirred for 30 min. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give the title compound (44.6 g, yield 83%) as a colorless oil. 1H NMR (CDCl3) δ: 1.23 (3H, t, J=7.2 Hz), 2.58 (2H, t, J=8.1 Hz), 2.89 (2H, t, J=8.1 Hz), 4.12 (2H, q, J=7.2 Hz), 6.51-6.56 (2H,m), 7.01-7.06 (1H, m).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. customThe organic layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ec70d35930ca45d9bdd437c7a36d0b55
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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