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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 2261804
Notes
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Reaction equation

HRID 2261804 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 675288602-Bromo-4-[1,3]dioxin-2-yl-benzoic acid methyl esterHCID 178445883HCID 178445883, compound

Product 1

HCID 675283664-[1,3]Dioxin-2-yl-2-pentyl-benzoic acid methyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst
HCID 8028
Tetrahydrofuran
Solvent

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

  1. temperatureAfter cooling to room temperature
  2. customthe mixture is partitioned between EtOAc (30 mL) and water (30 mL)
  3. washThe organic phase is washed with brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a residue
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes