Sodium hydride → Methyl 3-fluoro-4-(oxetan-3-yloxy)benzoate

HRID 1908105

Reaction equation

[H-].[Na+].[O:3]1[CH2:6][CH:5]([OH:7])[CH2:4]1.[F:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1F)[C:12]([O:14][CH3:15])=[O:13]>CN(C=O)C>[F:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[O:7][CH:5]1[CH2:6][O:3][CH2:4]1)[C:12]([O:14][CH3:15])=[O:13]

Participants

Conditions

Temperature: 80 °C

Procedure

NaH (80 mg, 2.0 mmol) was added to a mixture of oxetan-3-ol (150 mg, 2.0 mmol) and DMF (2 mL) at 0° C. The reaction was allowed to stir for 10 minutes before methyl 3,4-difluorobenzoate (170 mg, 1.0 mmol) was added. The reaction was then heated at 80° C. overnight. The reaction was quenched with brine and was extracted with EtOAc (3×). The combined organic layers were dried over sodium sulfate and the solvent was removed to give methyl 3-fluoro-4-(oxetan-3-yloxy)benzoate. ESI-MS m/z calc. 226.1. found 227.2 (M); Retention time: 2.36 minutes (4 min run).

Workup

additionwas added
customThe reaction was quenched with brine
extractionwas extracted with EtOAc (3×)
dry with materialThe combined organic layers were dried over sodium sulfate
customthe solvent was removed

Sources & evidence

ORD record: ord-8ced84a66f6348e58bdd26148c0a008a
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Linked notes

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