Ethyl Acetate → HCID 86693517, compound

HRID 575455Notes

Reaction equation

HRID 575455 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([OH:16])[CH2:13][C:14]#[CH:15].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH2:12]([O:16][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[CH2:13][C:14]#[CH:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 135663-Butyn-1-OLHCID 145905821-Fluoro-4-iodo-2-nitrobenzene

Product 1

HCID 86693517HCID 86693517, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-fluoro-4-iodo-2-nitro-benzene (5.0 g, 0.02 mol), 3-butyn-1-ol (1.57 ml, 0.02 mol) and potassium carbonate (2.86 g, 0.02 mol) in N,N-dimethylformamide (20 ml) was heated to 100° C. for 18 hours. After cooling the mixture was distributed between ethyl acetate (400 ml) and water (100 ml). The organic layer was separated, washed with water (2×100 ml) and brine (100 ml), dried over MgSO4, filtered and pre-absorbed onto a small amount of silica. Purification by FCC (silica, 0-15% ethyl acetate in heptanes) provided 3.7 g (56%) of the title compound. 1H NMR (250 MHz, CDCl3) 8 ppm 2.06 (1H, t, J=2.66 Hz), 2.75 (2H, td, J=7.16, 2.74 Hz), 4.22 (2H, t, J=7.08 Hz), 6.88 (1H, d, J=8.83 Hz), 7.81 (1H, dd, J=8.83, 2.28 Hz), 8.11 (1H, d, J=2.28 Hz).

Workup

  1. temperatureAfter cooling the mixture
  2. customThe organic layer was separated
  3. washwashed with water (2×100 ml) and brine (100 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. custompre-absorbed onto a small amount of silica
  7. customPurification by FCC (silica, 0-15% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-e9a7d2fd5e5249d8a06449970fdc502c
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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