Ethyl Acetate → HCID 57969057, compound

HRID 1471619Notes

Reaction equation

HRID 1471619 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Br:11][C:12]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:13]=1[CH:14]=[O:15].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[Br:11][C:12]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:16][C:13]=1[CH:14]=[O:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 3871792-Bromo-5-hydroxybenzaldehyde

Product 1

HCID 57969057HCID 57969057, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-fluoro-4-nitro-benzene (1.1 mL, 10.0 mmol, 1.0 eq.), 2-bromo-5-hydroxy-benzaldehyde (2.0 g, 10.0 mmol, 1.0 eq.) in DMF (30.0 mL) was added K2CO3 (1.7 g, 12.0 mmol, 1.2 eq.) under nitrogen atmosphere. The mixture was heated at 100° C. overnight. After cooling to room temperature, the mixture was poured into EtOAc (30 mL) and sat. H2O (30 mL). The layers were separated and the aqueous phase was extracted with EtOAc (3×20 mL). Combined organic extracts was washed with brine (30 mL), dried over MgSO4, filtered and the filtrate was concentrated under reduced pressure. The residue was applied to silica chromatography eluting with EtOAc/Heptanes (0:100 to 100:0) to give 2-bromo-5-(4-nitro-phenoxy)-benzaldehyde as a yellow fine powder. 1H NMR (CHLOROFORM-d) δ: 10.31-10.37 (m, 10H), 8.26 (dd, J=9.0, 0.3 Hz, 15H), 8.21-8.28 (m, 13H), 7.73 (d, J=8.6 Hz, 3H), 7.73 (dt, J=8.7, 0.5 Hz, 7H), 7.62 (dd, J=3.1, 0.3 Hz, 10H), 7.20-7.29 (m, 19H), 7.00-7.10 (m, 23H). Amount obtained, 2.6 g, 80.7% yield.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with EtOAc (3×20 mL)
  4. washCombined organic extracts was washed with brine (30 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washeluting with EtOAc/Heptanes (0:100 to 100:0)

Sources & evidence

ORD record
ord-86236a148eff404dbb4840704a776c44
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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