Water → Tributyl(5-fluorobenzofuran-2-yl)stannane

HRID 1822796Notes

Reaction equation

HRID 1822796 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][CH:13]=[CH:12][C:11]=2[CH:15]=1.[CH2:16]([Sn:20](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].O>C1COCC1>[CH2:25]([Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:21][CH2:22][CH2:23][CH3:24])[C:13]1[O:14][C:10]2[CH:9]=[CH:8][C:7]([F:6])=[CH:15][C:11]=2[CH:12]=1)[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 117883225-Fluoro-1-benzofuranHCID 178418339Butyllithium

Product 1

HCID 22170021Tributyl(5-fluorobenzofuran-2-yl)stannaneYield 22.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Butyllithium (1.5 mL, 2.4 mmol, 1.6 M) was added at −75° C. to a solution of 5-fluorobenzofuran (0.3 g, 2.2 mmol) in THF (10 mL). Tributyltin chloride (0.98 g, 1 mL) was added at −75° C. and the mixture was allowed to warm to 25° C. over a period of 2 hours. Water (25 mL) was added and the aqueous layer was extracted with diethyl ether (2×25 mL). The combined organic extracts were dried over Na2SO4 and concentrated. Silica gel chromatography (pentane) provided tributyl-(5-fluorobenzofuran-2-yl)-stannane (210 mg).

Workup

  1. extractionthe aqueous layer was extracted with diethyl ether (2×25 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-441fa31fdc6241acb722b4f0197bb243
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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