Water → HCID 118022789, compound

HRID 518558Notes

Reaction equation

HRID 518558 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]Cl)[CH:5]=[CH:4][C:3]=1[O:10][CH2:11][C:12]([F:15])([F:14])[F:13].[Na+].[I-].[CH3:18][CH2:19][SH:20].O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][S:20][CH2:19][CH3:18])[CH:5]=[CH:4][C:3]=1[O:10][CH2:11][C:12]([F:15])([F:14])[F:13]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6343EthanethiolHCID 63052156HCID 63052156, compound

Product 1

HCID 118022789HCID 118022789, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of the title compound from Step 3 (2.00 g, 6.59 mmol) in DCM (200 mL) was added TEA (1 g, 9.89 mmol), NaI (898 mg, 5.99 mmol) and EtSH (613 mg, 9.89 mmol). The mixture was stirred at 30° C. for 4 hrs. The reaction was poured into water (10 mL) and extracted with EtOAc (10 mL×3). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2SO4 and filtered. Solvents were removed under reduced pressure and the residue was purified by silica gel chromatography (PE:EA=1:0˜3:1) to give the title compound (2.1 g, 96.8%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.55 (d, J=2.0 Hz, 1 H), 7.24 (dd, J1=8.4 Hz, J2=2.0 Hz, 1H), 6.89 (d, J=8.4 Hz, 1H), 4.42 (q, J=8.0 Hz, 2H), 3.66 (s, 2H), 2.47-2.41 (m, 2H), 1.26-1.22 (m, 3H).

Workup

  1. extractionextracted with EtOAc (10 mL×3)
  2. washThe combined organic layers were washed with brine (30 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customSolvents were removed under reduced pressure
  6. customthe residue was purified by silica gel chromatography (PE:EA=1:0˜3:1)

Sources & evidence

ORD record
ord-c98dd2655e02491d9f351e6f879fd566
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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