Sodium Sulfite → 4-Chloro-2-(4-hydroxy-phenyl)-7-methoxy-benzofuran-5-ol

HRID 1836005Notes

Reaction equation

HRID 1836005 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:16]([O:17][CH3:18])=[CH:15][C:14]([OH:19])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1.C1C(=O)N([Cl:27])C(=O)C1.[O-]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>CC#N.[Cl-].[Na+].O>[Cl:27][C:13]1[C:11]2[CH:12]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)[O:9][C:10]=2[C:16]([O:17][CH3:18])=[CH:15][C:14]=1[OH:19]

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 102860222-(4-Hydroxy-phenyl)-7-methoxy-benzofuran-5-ol

Product 1

HCID 101930274-Chloro-2-(4-hydroxy-phenyl)-7-methoxy-benzofuran-5-olYield 22.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Compound 62 (0.1 g, 0.39 mmol) in CH3CN (10 mL) was treated with portionwise addition of NCS (0.033 g, 0.24 mmol). After addition, 10% Na2SO3 aq was added followed by NaHCO3 and brine. The EtOAc layer was dried over MgSO4, filtered, concentrated and chromatographed on silica gel (3:7 EtOAc/hexanes) to yield 0.016 g of the product: Mp=176-177° C.; 1H NMR (DMSO-d6) δ 9.89 (br s, 2 H), 7.74 (d, 2 H, J=8.6 Hz), 7.10 (s, 1 H), 6.87 (d, 2 H, J=8.7 Hz), 6.55 (s, 1 H), 3.91 (s, 3 H); MS 291 (M+H)+.

Workup

  1. additionwas added
  2. dry with materialThe EtOAc layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel (3:7 EtOAc/hexanes)

Sources & evidence

ORD record
ord-7891e2416ee04342a59dff9ef27c96f3
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

Loading…