3-Iodobenzaldehyde → HCID 59305345, compound

HRID 2240930Notes

Reaction equation

HRID 2240930 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10]([Mg]Br)[CH2:11][CH:12]=[CH2:13]>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH2:13][CH2:12][CH:11]=[CH2:10])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 2526103-IodobenzaldehydeHCID 178418797HCID 178418797, compound

Product 1

HCID 59305345HCID 59305345, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

To a stirred solution of 3-iodo-benzaldehyde (3.0 g, 12.93 mmol) in dry THF (45 mL) at −78° C. under nitrogen was added 0.5 M 3-butenyl magnesium bromide in THF (25.86 mL, 12.93 mmol) over 20 min. The reaction was stirred for 0.5 h and allowed to warm to −30° C. over 1 h and then quenched with sat ammonium chloride (20 mL). The reaction was diluted with water (10 mL) and then extracted with ethyl acetate (2×50 mL). The extracts were dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (5% to 10% ethyl acetate/petroleum ether) gave the title compound as a clear oil (3.5 g, 95%) and was used directly in the next step.

Workup

  1. customquenched with sat ammonium chloride (20 mL)
  2. additionThe reaction was diluted with water (10 mL)
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (5% to 10% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-c59e6ed4d1b54db88c2930669fa43267
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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