Dimethylformamide → 5-Bromo-2,4-difluorobenzaldehyde

HRID 523570Notes

Reaction equation

HRID 523570 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[C:5]([F:9])=[CH:4][C:3]=1[F:10].CN([CH:14]=[O:15])C.C([Li])CCC>CCOCC>[Br:8][C:6]1[C:5]([F:9])=[CH:4][C:3]([F:10])=[C:2]([CH:7]=1)[CH:14]=[O:15]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 105645111,5-Dibromo-2,4-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 222607695-Bromo-2,4-difluorobenzaldehydeYield 61.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 27 for the preparation of I-27a above, 1,5-dibromo-2,4-difluorobenzene (3 g, 11.07 mmol) in dry ether was reacted with DMF (1.05 mL, 14.39 mmol) and n-butyl lithium (6.08 ml, 11.56 mmol to afford the crude product. Purification by column chromatography on silica gel (2% ethyl acetate in hexane) afforded 1.5 g of the product (61% yield).

Workup

  1. customreagents and reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (2% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-167eff5df4844b98b424a05f4c65a53d
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

Loading…