Potassium Carbonate → N-[2-Fluoro-6-(2-oxiranylmethoxy)phenyl]acetamide

HRID 1393051Notes

Reaction equation

N[C:2]1[C:7](F)=CC=C[C:3]=1[OH:9].[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:12]=1[NH:18][C:19](=[O:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+].C(C1OC1)Br>O.CO.CN(C=O)C.C(OCC)(=O)C.O>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:7][CH:2]2[CH2:3][O:9]2)[C:12]=1[NH:18][C:19](=[O:21])[CH3:20]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 2-amino-3-fluorophenol (300 mg, 2.36 mmol) in water-methanol (10 ml) acetic acid anhydride was added until all 2-amino-3-fluorophenol was used. The solution was then concentrated to a residue of N-(2-fluoro-6-tiydroxyphenyl) acetamide. To a mixture of N-(2-fluoro-6-hydroxyphenyl) acetamide (399 mg, 2.36 mmol) and potassium carbonate (652 mg, 4.72 mmol) in DMF (5 ml) was added epibromohydrin (388 mg, 2.8 mmol) and was stirred at 70° C. for 3 hrs. Water and ethyl acetate were added. the organic phase separated, dried and concentrated. The resulting residue was purified by RP-HPLC (10-40% CH3CN ) to give the desired product as a solid (242 mg, 1.08 mmol).

Workup

concentrationThe solution was then concentrated to a residue of N-(2-fluoro-6-tiydroxyphenyl) acetamide
customthe organic phase separated
customdried
concentrationconcentrated
customThe resulting residue was purified by RP-HPLC (10-40% CH3CN )

Sources & evidence

ORD record: ord-c282500ca1cd460fb5330ab0fbe7e000
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345063B2

Reaction notes

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