Dimethylformamide → HCID 77174822, compound

HRID 2189145Notes

Reaction equation

HRID 2189145 reaction equation
C([Li])CCC.[Br:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([F:14])=[CH:9][C:8]=1I.CN(C)[CH:18]=[O:19].C(OC)(C)(C)C>O1CCCC1.O>[Br:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([F:14])=[CH:9][C:8]=1[CH:18]=[O:19]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 15413tert-Butyl methyl etherHCID 509980801-Bromo-5-chloro-4-fluoro-2-iodobenzeneHCID 178418339Butyllithium

Product 1

HCID 77174822HCID 77174822, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1 mmol of n-butyllithium (1N in hexane) is added dropwise to a solution of 1 mmol of 1-bromo-5-chloro-4-fluoro-2-iodo-benzene in 20 ml of tetrahydrofuran cooled to −78° C. After the addition, 1.1 mmol of N,N-dimethylformamide is added and the mixture is allowed to warm to room temperature. 100 ml of tert-butylmethyl ether then 20 ml of water are added. The organic phase is separated, washed with 20 ml of brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title compound which is identified based on the Rf value.

Workup

  1. additionis added
  2. temperatureto warm to room temperature
  3. customThe organic phase is separated
  4. washwashed with 20 ml of brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-9bd65d72eb75415199fdea3ad293c960
Source dataset
uspto-grants-2012_12
Patent number
US08324235B2

Reaction notes

Loading…