3-(Trifluoromethyl)phenol → 4-(3-(Trifluoromethyl)phenoxy)benzaldehyde

HRID 536168Notes

Reaction equation

HRID 536168 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([O:9][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 10796Cesium carbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 121487884-(3-(Trifluoromethyl)phenoxy)benzaldehydeYield 124.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(Trifluoromethyl)phenol (2.0 g, 12.34 mmol), 4-Fluorobenzaldehyde (2.0 g, 16.11 mmol), and Cs2CO3 (5.0 g, 15.35 mmol) in N,N-Dimethylformamide (DMF) (20 mL) was heated at 100° C. for 2 h, then cooled to rt. The solid suspension was removed by filtration over silica pad, and concentrated to afford crude title product (4.1 g) as a yellow liquid. LC-MS (ESI): m/z 267 [M+H]+; 3.60 min (ret time).

Workup

  1. customThe solid suspension was removed by filtration over silica pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7b7d0f2c226642c48b0374692e548ccc
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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