Dimethylformamide → 4-Bromo-2,6-difluorobenzaldehyde

HRID 523560Notes

Reaction equation

HRID 523560 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[CH:3]=1.CN([CH:13]=[O:14])C.C([Li])CCC.C(NC(C)C)(C)C>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH:13]=[O:14])=[C:4]([F:9])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 1363131-Bromo-3,5-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 27732904-Bromo-2,6-difluorobenzaldehydeYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using analogous reaction condition and reagents as described in Example 20 for the preparation of I-20a above, 1-bromo-3,5-difluoro-benzene (2 g, 2.10.36 mmol) in THF was reacted with DMF (1.43 g, 19.68 mmol), n-butyl lithium (1.56 ml, 12.4 mmol) and diisopropyl amine (0.57 mL, 15.5 mmol) to afford crude product. Purification by column chromatography on silica gel (2% ethyl acetate in hexane) afforded 1.35 g of the product (61% yield).

Workup

  1. customto afford crude product
  2. customPurification by column chromatography on silica gel (2% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-829826c63a8c481fa3d5815135a8655c
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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