Water → HCID 86711831, compound

HRID 623742Notes

Reaction equation

HRID 623742 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](I)[CH2:9][S:10]([C:13]2[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[C:4]([F:21])[CH:3]=1.CCN(CC)CC.OS([O-])(=O)=O.[Na+].O>CCOCC.C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[S:10]([C:13]2[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[C:4]([F:21])[CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 516919Sodium BisulfateHCID 86711830HCID 86711830, compound

Product 1

HCID 86711831HCID 86711831, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Crude 4-chloro-2-fluoro-1-(1-iodo-2-tosylethyl)benzene (51.8 g, max. 154 mmol) was dissolved in a mixture of Et2O (250 mL), THF (50 mL) and EtOAc (80 mL) after some warming. Carefully, Et3N (23.6 mL, 170 mmol) was added in 2 mL portions at room temperature. The mixture was stirred for 90 min at room temperature. Aqueous 1 M NaHSO4 (200 mL) and H2O (100 mL) were added and the organic layer was separated. The aqueous layer was extracted with EtOAc (50 mL). The combination of organic layers was washed with saturated aqueous NaHCO3 and with brine, dried (Na2SO4) and filtered. The solvent was evaporated in vacuo to give a yellow solid. The residue was triturated in MeOH (50 mL), filtration and air-drying provided 23.04 g (48% over two steps) of the desired product as a white solid.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with EtOAc (50 mL)
  3. washThe combination of organic layers was washed with saturated aqueous NaHCO3 and with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe solvent was evaporated in vacuo
  7. customto give a yellow solid
  8. customThe residue was triturated in MeOH (50 mL)
  9. filtrationfiltration
  10. customair-drying

Sources & evidence

ORD record
ord-79511c4a5b604c2394d3cf5bcedb1813
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

Loading…