Triphenylphosphine → Methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate

HRID 395203Notes

Reaction equation

O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[CH:22]([CH3:24])[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:44]N1C(=O)CCC1=O>C(Cl)Cl>[Br:44][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[CH:22]([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of methyl [4-(4-hydroxymethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate (Compound 123, 180.0 mg, 0.56 mmol) and triphenylphosphine (190.0 mg, 0.73 mmol) in 5 mL CH2Cl2 was cooled to 0° C. and N-bromosuccinimide (130.0 mg, 0.73 mmol) was added in 5 portions over 20 minutes. The solution was warmed to 25° C. and stirred for 17 hours. The reaction was quenched by the addition of dilute aqueous NaHCO3. The resulting mixture was extracted with Et2O and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (Na2SO4) and concentrated under reduced pressure. The title compound, 212.0 mg (98%), was isolated by column chromatography (5-10% EtOAc-hexanes) as a pale-yellow oil.

Workup

customThe reaction was quenched by the addition of dilute aqueous NaHCO3
extractionThe resulting mixture was extracted with Et2O
washthe combined organic layers were washed with H2O and saturated aqueous NaCl
dry with materialbefore being dried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-20f18824f281489d9c6e11f4593dffe2
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06603019B2

Reaction notes

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