Iodine → HCID 67512931, compound

HRID 1508485Notes

Reaction equation

HRID 1508485 reaction equation
II.FC(F)(F)C(O[I:8](C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:36]=[C:35]([C:37]([O:39][CH3:40])=[O:38])[O:34][N:33]=2)=[CH:28][CH:27]=1>C(Cl)Cl>[I:8][C:31]1[CH:30]=[C:29]([C:32]2[CH:36]=[C:35]([C:37]([O:39][CH3:40])=[O:38])[O:34][N:33]=2)[CH:28]=[CH:27][C:26]=1[O:25][CH3:24]

Participants

5

Reactant 3

HCID 807IodineHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 776534HCID 776534, compound

Product 1

HCID 67512931HCID 67512931, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodine (0.147 mL, 2.85 mmol) and [bis(trifluoroacetoxy)iodo]benzene (1.224 g, 2.85 mmol) were added successively to a solution of methyl 3-(4-methoxyphenyl)isoxazole-5-carboxylate (1.021 g, 4.38 mmol) in CH2Cl2 (13.2 mL) at 25° C. and the reaction was stirred overnight. After this time the solvent was removed 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, gradient to 40% EtOAc in hexanes over 2448 mL) to afford methyl 3-(3-iodo-4-methoxyphenyl)isoxazole-5-carboxylate, as a colorless oil. LCMS calc.=359.97. found=359.81 (M+H)+. 1H NMR (600 MHz, CDCl3): δ 8.24 (d, J=2.1 Hz, 1H); 7.78 (dd, J=8.5, 2.2 Hz, 1H); 7.19 (s, 1H); 6.89 (d, J=8.5 Hz, 1H); 3.99 (s, 3H); 3.93 (s, 3H).

Workup

  1. customAfter this time the solvent was removed in vacuo
  2. customto give the crude product
  3. 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, gradient to 40% EtOAc in hexanes over 2448 mL)

Sources & evidence

ORD record
ord-47bf9d6e4ca54ea29c59e237d3c62d3e
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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