2-Bromo-4-[1,3]dioxin-2-yl-benzoic acid methyl ester → 4-[1,3]Dioxin-2-yl-2-pentyl-benzoic acid methyl ester

HRID 2261804Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[O:15][CH2:14][CH:13]=[CH:12][O:11]2)=[CH:6][C:5]=1Br.[Br-].[CH2:19]([Zn+])[CH2:20][CH2:21][CH2:22][CH3:23]>C1COCC1.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]>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[O:15][CH2:14][CH:13]=[CH:12][O:11]2)=[CH:6][C:5]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: 50 °C

Procedure

To a degassed solution of 2-bromo-4-[1,3]dioxin-2-yl-benzoic acid methyl ester (380 mg, 1.3 mmol) in THF (10 mL) are added PdCl2(dppf)2 (108 mg, 0.13 mmol) and n-pentyl zinc bromide (0.5 M in THF, 8.0 mL, 4.0 mmol). The mixture is heated to 50° C. overnight. After cooling to room temperature, the mixture is partitioned between EtOAc (30 mL) and water (30 mL). The organic phase is washed with brine (30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to afford the title compound as syrup (360 mg, 98%). LC-ES/MS m/e 279.3 (M+1).

Workup

temperatureAfter cooling to room temperature
customthe mixture is partitioned between EtOAc (30 mL) and water (30 mL)
washThe organic phase is washed with brine (30 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure to a residue
customThe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-e8854be33352401c9a5662a6d43660b0
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846960B2

Reaction notes

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