Sulfuric Acid → HCID 58042300, compound

HRID 1619661Notes

Reaction equation

HRID 1619661 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1.[I:19]N1C(=O)CCC1=O.S(=O)(=O)(O)O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([I:19])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 120273N-Iodosuccinimide2×HCID 58042336HCID 58042336, compound

Product 1

HCID 58042300HCID 58042300, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloro-3′-(trifluoromethyl)biphenyl-4-ol (Preparation 50, 310 mg, 1.14 mmol) was dissolved in acetic acid (2 mL), and cooled to 0° C. N-iodosuccinimide (256 mg, 1.14 mmol) was added followed by concentrated sulphuric acid (0.067 μL). The reaction was stirred at room temperature for 18 hours. A second portion of N-iodosuccinimide (25 mg, 0.11 mmol) was added and the reaction stirred at room temperature for a further 1 hour. The reaction mixture was partitioned between ethyl acetate (70 mL) and water (50 mL). The ethyl acetate was separated, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica eluting with a gradient of heptane:ethyl acetate 100:0 to 80:20 to give the title compound (230 mg, 0.58 mmol, 51%) as a white solid.

Workup

  1. stirringthe reaction stirred at room temperature for a further 1 hour
  2. customThe reaction mixture was partitioned between ethyl acetate (70 mL) and water (50 mL)
  3. customThe ethyl acetate was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on silica eluting with a gradient of heptane:ethyl acetate 100:0 to 80:20

Sources & evidence

ORD record
ord-95d8550c049048af85f3e4a7b0fbc5aa
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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