Iodine → HCID 121004314, compound

HRID 1508474Notes

Reaction equation

HRID 1508474 reaction equation
[I:1]I.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:13][C@@H:12]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][CH:6]=1>CCO.S([O-])([O-])(=O)=O.[Ag+2]>[I:1][C:10]1[CH:9]=[C:8]([C@H:11]2[CH2:13][C@@H:12]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=[CH:6][C:5]=1[O:4][CH3:3]

Participants

5

Reactant 2

HCID 807IodineHCID 818083HCID 818083, compound

Product 1

HCID 121004314HCID 121004314, compound

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

Silver sulfate (3.47 g, 11.12 mmol) and iodine (0.576 mL, 11.12 mmol) were added successively to a solution of ethyl (1S,2S)-2-(4-methoxyphenyl)cyclopropanecarboxylate (2.45 g, 11.12 mmol) in EtOH (55.6 mL) at 25° C. and the reaction was stirred vigorously for 4 h. After this time the reaction mixture was filtered through a plug of Celite®. The filtrate was diluted with EtOAc (100 mL), washed with water (2×25 mL), aq. NaHSO3 (2×25 mL), and brine (25 mL), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 20% EtOAc in hexanes over 2088 mL) to afford ethyl (1S,2S)-2-(3-iodo-4-methoxyphenyl)cyclopropanecarboxylate, as a colorless oil. Rf=0.61 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3): δ 7.50 (d, J=2.3 Hz, 1H); 7.04 (dd, J=8.5, 2.3 Hz, 1H); 6.71 (d, J=8.5 Hz, 1H); 4.15 (q, J=7.2 Hz, 2H); 3.83 (s, 3H); 2.44-2.39 (m, 1H); 1.82-1.78 (m, 1H); 1.55-1.50 (m, 1H); 1.27 (t, J=7.2 Hz, 3H); 1.25-1.19 (m, 1H).

Workup

  1. filtrationAfter this time the reaction mixture was filtered through a plug of Celite®
  2. additionThe filtrate was diluted with EtOAc (100 mL)
  3. washwashed with water (2×25 mL), aq. NaHSO3 (2×25 mL), and brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThis was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 20% EtOAc in hexanes over 2088 mL)

Sources & evidence

ORD record
ord-2a49e1809913433a86b378a7440cdfa4
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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