N-Iodosuccinimide → 2-Chloro-2'-fluoro-4-iodo-5-methoxybiphenyl

HRID 1619696Notes

Reaction equation

HRID 1619696 reaction equation
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24]>S(=O)(=O)(O)O.C(O)(=O)C.ClCCl>[Cl:9][C:10]1[CH:15]=[C:14]([I:1])[C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24]

Participants

6

Reactant 2

HCID 120273N-IodosuccinimideHCID 580422982-Chloro-2'-fluoro-5-methoxybiphenyl

Product 1

HCID 580423152-Chloro-2'-fluoro-4-iodo-5-methoxybiphenylYield 60.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

N-Iodosuccinimide (683 mg, 3.04 mmol) was added to a solution of 2-chloro-2′-fluoro-5-methoxybiphenyl (Preparation 96, 749 mg, 3.16 mmol) in concentrated sulfuric acid (0.09 mL), acetic acid (4.7 mL) and dichloromethane (4.7 mL). The resulting mixture was stirred at room temperature for 18 hours and then partitioned between dichloromethane (30 mL) and water (5 mL). The organic phase was separated and washed with water (2×5 mL), brine (5 mL), dried over MgSO4, filtered and evaporated to give a red oil. Column chromatography purification on silica, eluting with dichloromethane:heptanes (1:9) gave the title compound (671 mg, 58%) as a colourless oil.

Workup

  1. custompartitioned between dichloromethane (30 mL) and water (5 mL)
  2. customThe organic phase was separated
  3. washwashed with water (2×5 mL), brine (5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a red oil
  8. customColumn chromatography purification on silica
  9. washeluting with dichloromethane:heptanes (1:9)

Sources & evidence

ORD record
ord-d62db1b14fc1499eb54ec3a4b2cc7148
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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