Trifluoroacetic acid → 2-Fluoro-1-isopropyl-4-methoxybenzene

HRID 2283144Notes

Reaction equation

HRID 2283144 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](O)([CH3:12])[CH3:11].C1(SC2C=CC=CC=2)C=CC=CC=1.C(O)(C(F)(F)F)=O>[Pd]>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8766Diphenyl sulfideHCID 134938442-(2-Fluoro-4-methoxyphenyl)-2-propanol

Product 1

HCID 206055182-Fluoro-1-isopropyl-4-methoxybenzene

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The solution of 2-(2-fluoro-4-methoxyphenyl)propan-2-ol in IPAC (500 ml, 451 mmol) and diphenyl sulfide (0.151 ml, 0.901 mmol) were combined in a hydrogenation shaker. The reaction mixture was purged with nitrogen/vacuum cycles, and 5% palladium on carbon (7.67 g, 1.802 mmol) was added, followed by TFA (17.36 ml, 225 mmol). Hydrogenation was conducted at 60° C. under 50 psig pressures for 12 h. The catalyst was removed by filtration through a 1 inch plug of Solka-Floc® powdered cellulose and rinsed with IPAC (49.8 ml). The filtrate was assayed and was found to contain 76 g of the desired product, which corresponds to a quantitative yield.

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration through a 1 inch plug of Solka-Floc®
  3. washrinsed with IPAC (49.8 ml)

Sources & evidence

ORD record
ord-9c1f0a3d99a344d5b4adff7c96dddbdf
Source dataset
uspto-grants-2015_09
Patent number
US09145348B2

Reaction notes

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