2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → (5-Methoxybenzofur-7-yl)acetic acid ethyl ester

HRID 751501Notes

Reaction equation

HRID 751501 reaction equation
Br[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([O:11][CH3:12])[CH:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.[Br-].[CH2:42]([O:44][C:45](=[O:48])[CH2:46][Zn+])[CH3:43]>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH2:42]([O:44][C:45](=[O:48])[CH2:46][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([O:11][CH3:12])[CH:3]=1)[CH3:43]

Participants

6

Reactant 3

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 221447037-Bromo-5-methoxy-1-benzofuranHCID 178472538HCID 178472538, compound

Product 1

HCID 69266596(5-Methoxybenzofur-7-yl)acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

Dissolve 7-bromo-5-methoxybenzofuran (6.0 g, 26.43 mmol), bis(dibenzylideneacetone)palladium (1.32 g, 2.3 mmol) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (2.7 g, 6.86 mmol) in anhydrous tetrahydrofuran (36 mL), add freshly prepared 2-ethoxy-2-oxoethylzinc bromide in tetrahydrofuran (66 mL). Heat at 50-60° C. for 5 h. Cool and filter mixture through celite and evaporate to a thick red-brown oil (30 g). Purify by flash chromatography using a gradient of ethyl acetate in hexanes yields the pure compound as a thick yellow oil (6.2 g, quant). ESMS m/z (relative intensity) 235.2 (M++H+, 10), 161.1 (M+−CO2Et+H+, 100).

Workup

  1. temperatureCool
  2. filtrationfilter mixture through celite
  3. customevaporate to a thick red-brown oil (30 g)
  4. customPurify by flash chromatography

Sources & evidence

ORD record
ord-05e41b7aa88645289a51ffb67c72f036
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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