18-Crown-6 → HCID 57466786, compound

HRID 558118Notes

Reaction equation

HRID 558118 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:14])[C:10]([F:13])([F:12])[F:11].C1OCCOCCOCCOCCOCCOC1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:14])[C:10]([F:11])([F:12])[F:13]

Participants

4

Reactant 2

HCID 2855718-Crown-6HCID 57445066HCID 57445066, compound

Product 1

HCID 57466786HCID 57466786, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add 1-(2-bromo-4-fluoro-phenyl)-2,2,2-trifluoro-ethanol (12 g, 43.9 mmol) in 20 mL DCM to a stirred suspension solution of 3,3,3-triacetoxy-3-iodophthalide (52 g, 122.6 mmol) and 18-crown-6 (0.6 g) in DCM (400 mL). Stir the mixture at RT for 4 h and pour into a solution of NaHCO3/NaS2O3. Wash the organic layer with water, dry over sodium sulfate, and concentrate in vacuo. Purify the resulting crude product by FCC (20% ethyl acetate in hexane as the eluant) to give the title compound as a pale yellow oil (9 g, 76%). 1H NMR (400 MHz, CDCl3) δ 7.77 (m, 1H), 7.51 (m, 1H), 7.20 (m, 1H).

Workup

  1. washWash the organic layer with water
  2. dry with materialdry over sodium sulfate
  3. concentrationconcentrate in vacuo
  4. customPurify the resulting crude product by FCC (20% ethyl acetate in hexane as the eluant)

Sources & evidence

ORD record
ord-2c9a897dae5f4086bdf5968d278a3101
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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