4-Bromophenol → Ethyl 1-((4-bromophenoxy)methyl)cyclobutanecarboxylate

HRID 594866Notes

Reaction equation

CS([O:5][CH2:6][C:7]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][CH2:8]1)(=O)=O.[Br:16][C:17]1[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([O:5][CH2:6][C:7]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][CH2:8]2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 135 °C

Procedure

The mixture of ethyl 1-{[(methylsulfonyl)oxy]methyl}cyclobutanecarboxylate (1.50 g, 6.3 mmol), 4-bromophenol (1.2 g, 7.0 mmol), and caesium carbonate (4.13 g, 7.0 mmol) in DMF (15 ml) was stirred for 6 hours at 135° C. After dilution with EtOAc and H2O, the organic layer was washed with H2O, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (hexane:EtOAc=100:0-70:30) to give ethyl 1-[(4-bromophenoxy)methyl]cyclobutanecarboxylate (919 mg).

Workup

washAfter dilution with EtOAc and H2O, the organic layer was washed with H2O
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (hexane:EtOAc=100:0-70:30)

Sources & evidence

ORD record: ord-07cd15ed267d417abc6ffb36670e8099
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242973B2

Reaction notes

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