1-Bromo-2-Chloroethane → HCID 59632103, compound

HRID 2369046Notes

Reaction equation

HRID 2369046 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:18][CH2:19][Cl:20].[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH2:18][CH2:19][Cl:20])[N:11]=[C:10]([C:13]([F:14])([F:16])[F:15])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 178506069HCID 178506069, compound

Product 1

HCID 59632103HCID 59632103, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 5-(4-bromophenyl)-3-(trifluoromethyl)-1H-pyrazole (2.05 g, 7 mmol) and 1-bromo-2-chloroethane (0.71 mL, 1.2 equiv) in DMF (30 mL) was added NaH (0.42 g, 60%, 1.5 equiv) and the mixture was stirred overnight at 20° C. The reaction was quenched by water. Solid was collected and washed by water and dried under high vacuum to give a crude, which was purified by column chromatography eluting with MeOH-DCM (6:96) to give 5-(4-bromophenyl)-1-(2-chloroethyl)-3-(trifluoromethyl)-1H-pyrazole (400 mg) as a minor product. 1H-NMR (CDCl3): δ 7.64 (d, 1H), 7.31 (d, 1H), 6.54 (s, 1H), 4.41 (t, 2H), 3.93 (t, 2H).

Workup

  1. customThe reaction was quenched by water
  2. customSolid was collected
  3. washwashed by water
  4. customdried under high vacuum
  5. customto give a crude, which
  6. customwas purified by column chromatography
  7. washeluting with MeOH-DCM (6:96)

Sources & evidence

ORD record
ord-79e7d6ff7c2b4749afa55dc6223e321b
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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