Dimethylformamide → HCID 118045868, compound

HRID 595983Notes

Reaction equation

HRID 595983 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][F:9])[CH:5]=[C:4]([F:10])[CH:3]=1.C([Li])CCC.CN([CH:19]=[O:20])C>C1COCC1>[F:10][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH2:8][F:9])[CH:5]=1)[CH:19]=[O:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 118045958HCID 118045958, compoundHCID 178418339Butyllithium

Product 1

HCID 118045868HCID 118045868, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1-bromo-3-fluoro-5-(fluoromethyl)benzene (1.30 g, 6.28 mmol) was dissolved in THF (31.4 mL), then cooling down to −78° C., butyllithium (2.5M in Hexanes) (2.76 mL, 6.91 mmol) was added at −78° C., the reaction mixture was then stirred at −78° C. for 30 min. DMF (0.972 mL, 12.56 mmol) was added, after stirred at −78° C. for 1h, The reaction mixture was quenched by HCl and the reaction mixture was then extracted by EtOAc, the organic was dried and concentrated to yield the crude product. The crude material was used in next step reaction without purification. LCMS (m/z): no mass (MH+), 0.60 min. 1H NMR (400 MHz, CDCl3) δ ppm 10.08-9.93 (m, 1H), 7.68 (s, 1H), 7.56 (d, J=8.2 Hz, 1H), 7.37 (d, J=7.8 Hz, 1H), 5.53 (s, 1H), 5.42 (s, 1H)

Workup

  1. customThe reaction mixture was quenched by HCl
  2. extractionthe reaction mixture was then extracted by EtOAc
  3. customthe organic was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b92c05d9f5154dd7accca3eb57f589a8
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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