Tetrahydrofuran → 3-Bromo-5-(3-methoxypropyl)benzaldehyde

HRID 337594Notes

Reaction equation

HRID 337594 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.COCC=C.[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18](Br)[CH:19]=1)[CH:15]=[O:16].C[O-].[Na+]>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([CH2:2][CH2:1][CH2:5][O:4][CH3:3])[CH:19]=1)[CH:15]=[O:16]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 693921-Propene, 3-methoxy-HCID 6220773,5-DibromobenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 866516713-Bromo-5-(3-methoxypropyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Procedure

To a THF solution (0.3 M) of allyl methyl ether (3.1 eq.) at RT was added borane-methyl sulfide complex (1.0 eq.). The solution was stirred at RT for 30 min. To this solution was then added sequentially 3,5-dibromobenzaldehyde (1.0 eq.), Pd(dppf)Cl2 (0.025 eq.) and solid sodium methoxide (1.5 eq.). The resulting mixture was heated to reflux for 15 h. The cooled reaction mixture was diluted with water and extracted with ether. The combined organic extracts were dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 5:95 (v/v) EtOAc:Hex→7:3 (v/v) EtOAc:Hex) afforded the title compound as a colorless oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 15 h
  3. customThe cooled reaction mixture
  4. extractionextracted with ether
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, 5:95 (v/v) EtOAc:Hex→7:3 (v/v) EtOAc:Hex)

Sources & evidence

ORD record
ord-c80d014c2c464857ad4045dce4aa9992
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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