1,2-Dimethoxyethane → HCID 89464261, compound

HRID 2167118Notes

Reaction equation

HRID 2167118 reaction equation
Br[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].COCCOC>C(Cl)Cl>[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 15833211Methyl 2-Bromo-4-nitrobenzoate

Product 1

HCID 89464261HCID 89464261, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl 2-bromo-4-nitrobenzoate (5.20 g), 2-fluorophenylboronic acid (3.92 g) and potassium carbonate (4.98 g) in a 10:1 mixture of DME:water (120 ml) was degassed by gently bubbling though nitrogen for 30 minutes. Tetrakis(triphenylphosphine) palladium(0) (2.32 g) was then added and the mixture was degassed for a further 10 minutes before being sealed under nitrogen. The reaction mixture was heated to 100° C. for 14 hours. The solvents were removed under vacuum. The residue obtained was redissolved in DCM and washed with water (2×). The organic phase was passed through a hydrophobic frit and then concentrated to dryness under vacuum. The crude residue was purified by chromatography on silica gel, eluting with petrol containing increasing amounts of ethyl acetate.

Workup

  1. customwater (120 ml) was degassed
  2. customby gently bubbling though nitrogen for 30 minutes
  3. additionTetrakis(triphenylphosphine) palladium(0) (2.32 g) was then added
  4. customthe mixture was degassed for a further 10 minutes
  5. custombefore being sealed under nitrogen
  6. customThe solvents were removed under vacuum
  7. customThe residue obtained
  8. washwashed with water (2×)
  9. concentrationconcentrated to dryness under vacuum
  10. customThe crude residue was purified by chromatography on silica gel
  11. washeluting with petrol containing
  12. temperatureincreasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-4aa169857c554640a07b53de48834dd4
Source dataset
uspto-grants-2015_06
Patent number
US09044463B2

Reaction notes

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