Acetic Acid → HCID 117737283, compound

HRID 1504497Notes

Reaction equation

HRID 1504497 reaction equation
[F:1][CH:2]([F:19])[C:3]1[CH:4]=[C:5]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[F:18])[CH:6]=[C:7]([F:9])[CH:8]=1.S(=O)(=O)(O)O.CC(O)=O.C1C(=O)N([I:36])C(=O)C1>C(Cl)Cl>[F:19][CH:2]([F:1])[C:3]1[CH:4]=[C:5]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([I:36])=[CH:12][C:11]=2[F:18])[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 120273N-IodosuccinimideHCID 117737015HCID 117737015, compound

Product 1

HCID 117737283HCID 117737283, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 250-mL RBF was added 3′-(difluoromethyl)-2,5′-difluoro-5-methoxy-1,1′-biphenyl (642 mg, 2.376 mmol) and sulfuric acid (69.7 μl, 1.307 mmol). DCM (3960 μl) and AcOH (3960 μl) were added to give a colorless clear solution. To this solution was added n-iodosuccinimide (238 μl, 2.376 mmol) as a solid in a single portion to give a maroon-colored solution. After 3 h at rt, the mixture was diluted with DCM (30 mL), washed with water (10 mL), washed with saturated aq. sodium thiosulfate (10 mL, DCM was upper layer for separation), dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (50-g silica gel column, 0-5% EtOAc/Heptane) to provide 3′-(difluoromethyl)-2,5′-difluoro-4-iodo-5-methoxy-1,1′-biphenyl (771 mg, 1.946 mmol, 82% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.80-7.87 (m, 1H), 7.67-7.73 (m, 1H), 7.63-7.67 (m, 1H), 7.48-7.57 (m, 1H), 7.08-7.18 (m, 2H), 3.91 (d, J=2.54 Hz, 3H)

Workup

  1. customto give a colorless clear solution
  2. customto give a maroon-colored solution
  3. washwashed with water (10 mL)
  4. washwashed with saturated aq. sodium thiosulfate (10 mL, DCM was upper layer for separation)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (50-g silica gel column, 0-5% EtOAc/Heptane)

Sources & evidence

ORD record
ord-15f1d34ef3fc48d0b450928f2f668233
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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