Ethyl Acetate → 4-Benzyloxy-5'-isopropyl-2'-methoxy-biphenyl-2-carbaldehyde

HRID 604188Notes

Reaction equation

HRID 604188 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](Br)=[C:13]([CH:16]=1)[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18]([C:21]1[CH:22]=[CH:23][C:24]([O:30][CH3:31])=[C:25](B(O)O)[CH:26]=1)([CH3:20])[CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:16]=[C:13]([CH:14]=[O:15])[C:12]([C:25]2[CH:26]=[C:21]([CH:18]([CH3:20])[CH3:19])[CH:22]=[CH:23][C:24]=2[O:30][CH3:31])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 45891905-Isopropyl-2-methoxyphenylboronic acidHCID 108700245-(Benzyloxy)-2-bromobenzaldehyde

Product 1

HCID 866269194-Benzyloxy-5'-isopropyl-2'-methoxy-biphenyl-2-carbaldehydeYield 96.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

5-Benzyloxy-2-bromo-benzaldehyde (1.0 g) is dissolved in 1,4-dioxane (30 ml) and thereto are added [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium dichloromethane complex (280 mg), (5-isopropyl-2-methoxyphenyl)boronic acid (800 mg) and cesium carbonate (1.68 g) and the mixture is stirred under nitrogen atmosphere at 80° C. for 6 hours. The reaction mixture is cooled to room temperature, and thereto are added ethyl acetate and a saturated aqueous sodium bicarbonate solution, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1) to give 4-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-2-carbaldehyde (1.19 g). MS (m/z): 361 [M+H]+.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customa saturated aqueous sodium bicarbonate solution, and the mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-c283d116e10440b5bdb1bfced883d2e3
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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