Sodium Carbonate → HCID 21099398, compound

HRID 2376961Notes

Reaction equation

HRID 2376961 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)(=[O:10])=[O:9].[F:19][C:20]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:21]=1[CH2:22]P(=O)(OC)OC.C1OCCOCCOCCOCCOC1.[H-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:11]1[CH:18]=[CH:17][C:14](/[CH:15]=[CH:22]/[C:21]2[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:20]=2[F:19])=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 21099496HCID 21099496, compoundHCID 86225520HCID 86225520, compound

Product 1

HCID 21099398HCID 21099398, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

4-[(2-bromophenyl)sulfonyl]benzaldehyde (Step 4, 3.4 g, 10 46 mmol), dimethyl (2,4-difluorobenzyl)phosphonate (2.36 g, 11.51 mmol) and 15-crown-5 (0.23 mL, 1.15 mmol) were dissolved in tetrahydrofuran (21 mL) under nitrogen and cooled to 0° C. Sodium hydride (276 mg) was added and the reaction allowed to warm slowly to room temperature. Saturated sodium carbonate solution and ethyl acetate were added. The organic layer was washed with brine, dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 35% ethyl acetate/isohexane, to give 1-((E)-2-{4-[(2-bromophenyl)sulfonyl]phenyl}vinyl)-2,4-difluorobenzene as a white solid (3.1 g, 69%). δH (400 MHz, d6 DMSO): 8.33 (1H, dd, J=1.7, 7.9 Hz), 7.89-7.81 (6H, m), 7.72 (1H, td, J=1.2, 7.6 Hz), 7.62 (1H, td, J=1.8, 7.6 Hz), 7.45-7.35 (2H, m), 7.33-7.29 (1H, m), 7.16 (1H, td, J=2.5, 8.3 Hz).

Workup

  1. temperatureto warm slowly to room temperature
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with 35% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-8646f664f1c84805b5a1cf8dd603c23f
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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