3-Hydroxybenzaldehyde → 3-[(3-fluorobenzyl)oxy]benzaldehyde

HRID 710379Notes

Reaction equation

HRID 710379 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Cl.[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=[O:15].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=[O:15]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 99743-Fluorobenzyl chlorideHCID 10796Cesium carbonate

Product 1

HCID 8917113-[(3-fluorobenzyl)oxy]benzaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-fluorobenzyl chloride (0.71 g; 4.91 mmol), 3-hydroxybenzaldehyde (0.6 g; 4.91 mmol) and Cs2CO3 (1.6 g; 4.91 mmol) in anhydrous DMF (5 ml) was stirred for 4 h at ˜60° C. under N2, cooled to room temperature and poured onto H2O (15 ml). The precipitate formed was filtered off, washed with H2O and dried in vacuo to give the title compound (0.9 g; 80%), as creamy solid. 1H-NMR (CDCl3) 5.11 (s, 2H); 7.13-7.25 (m, 3H+CDCl3); 7.3-7.36 (m, 1H); 7.44-7.48 (m, 3H); 9.96 (5, 1H).

Workup

  1. temperaturecooled to room temperature
  2. additionpoured onto H2O (15 ml)
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. washwashed with H2O
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e153ed36fae447db8cccd87daf8d3588
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

Loading…