Methyl iodide → HCID 18687822, compound

HRID 1873211Notes

Reaction equation

HRID 1873211 reaction equation
IC.[Br:3][C:4]1[CH:9]=[C:8]([C:10]2[C:19]3[C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[S:22][C:18]=3[C:17]([Br:27])=[C:16]3[C:11]=2[CH:12]=[CH:13][CH:14]=[CH:15]3)[CH:7]=[C:6]([OH:28])[C:5]=1[OH:29].[C:30](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:3][C:4]1[C:5]([O:29][CH3:30])=[C:6]([OH:28])[CH:7]=[C:8]([C:10]2[C:19]3[C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[S:22][C:18]=3[C:17]([Br:27])=[C:16]3[C:11]=2[CH:12]=[CH:13][CH:14]=[CH:15]3)[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18687808HCID 18687808, compound

Product 1

HCID 18687822HCID 18687822, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (0.074 mL, 1.2 mmol) was added dropwise to a rt, stirred light suspension of 3-bromo-5-(6-bromo-benzo [b]naphtho [2,3 -d]thiophen-11 -yl)-benzene-1, 2-diol (0.30 g, 0.60 mmol), potassium carbonate (0.083 g, 0.6 mmol) in DMF (1.5 mL) over a period of five minutes. After the mixture was stirred at ambient temperature for 1.5 h., the reaction mixture was quenched with aqueous hydrochloric acid to pH 1 and further diluted with water (80 mL) and aqueous mixture was extracted with methylene chloride (120 mL). The organic extract was washed with water and dried with brine. Silica gel (5 mL) was added. Solvent was removed and the adsorbate was flash chromatographed (eluents:petroleum ether:methylene chloride 7:3 to 1:1 and then petroleum ether: ethyl acetate 7:3) to provide the title compound as a white solid (85 mg, 29%): mp 233-234° C.: NMR (CDCl3); δ8.35 (ddd, J=8, 1, 1 Hz, 1 H), 7.82 (ddd, J=8, 1, 1 Hz, 1 H), 7.66 (ddd, J=8, 7, 1 Hz, 1H), 7.65 (dd, J=8, 1, Hz, 1 H), 7.48 (ddd, J=8, 7, 1 Hz, 1 H), 7.43 (ddd, J=8, 7, 1 Hz, 1 H), 7.17 (ddd, J=8, 7, 1 Hz, 1 H), 7.15 (d, J=2 Hz, 1 H), 7.00 (d, J=2 Hz, 1 H), 6.87 (ddd, J=8, 1, 1 Hz, 1 H), 5.93 (s, 1 H), 4.14 (s, 3); MS (EI): [M+], 2 bromine isotope pattern, 512; Anal. Calc. for C23H14Br2O2S: C, 53.72, H, 2.74, N, 0.00. Found: C, 53.85, H, 2.98, N, 0.02.

Workup

  1. stirringAfter the mixture was stirred at ambient temperature for 1.5 h.
  2. customthe reaction mixture was quenched with aqueous hydrochloric acid to pH 1
  3. additionfurther diluted with water (80 mL) and aqueous mixture
  4. extractionwas extracted with methylene chloride (120 mL)
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialdried with brine
  8. additionSilica gel (5 mL) was added
  9. customSolvent was removed
  10. customchromatographed (eluents

Sources & evidence

ORD record
ord-0dde05a891ce42cfbb92a263a9afad99
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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