Triethylamine → 4-Bromo-2,6-difluorobenzaldehyde

HRID 389691Notes

Reaction equation

HRID 389691 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH2:6][OH:7])=[C:4]([F:11])[CH:3]=1.C(N(CC)CC)C>C(Cl)Cl.CS(C)=O.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([CH:6]=[O:7])=[C:8]([F:10])[CH:9]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 27733034-Bromo-2,6-difluorobenzyl alcohol

Product 1

HCID 27732904-Bromo-2,6-difluorobenzaldehydeYield 84%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2,6-difluorobenzylalcohol (0.200 g, 0.9 mmol) in DCM (4 ml) and DMSO (0.440 ml) was added triethylamine (1 ml, 0.72 mmol) and sulfur trioxide pyridine complex (0.570 g, 3.6 mmol) and the resulting solution was stirred at room temperature for 3 hours. The solution was diluted with Et2O and washed with 0.5M aqueous HCl, 1M sodium bicarbonate solution and brine. The organic phase was dried over MgSO4 and the solvent removed in vacuo to afford 4-bromo-2,6-difluorobenzaldehyde (0.166 g, 0.75 mmol, 84%) as a white solid. 1H NMR (CDCl3) δ 7.22 (2H, d), 10.29 (1H, br. s). LCMS (2) Rt: 2.74 min.

Workup

  1. washwashed with 0.5M aqueous HCl, 1M sodium bicarbonate solution and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-722468b6c01a423f988487eb31c55f56
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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