2-Fluoroaniline → Methyl 2-fluoro-4-[(2-fluoroanilino)methyl]benzoate

HRID 1497985Notes

Reaction equation

[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([F:27])[CH:18]=1>CN(C=O)C>[F:27][C:19]1[CH:18]=[C:17]([CH2:16][NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[F:1])[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2-fluoroaniline (0.12 mL, 1.2 mmol) and potassium carbonate (207 mg, 1.5 mL) in DMF (5 mL) was added methyl 4-(bromomethyl)-2-fluoro-benzoate (247 mg, 1 mmol). The mixture was heated to 60° C. for 18 hours. The solvent was removed in vacuo. The mixture was partitioned between DCM (15 mL) and water (15 mL), the layers were separated and the organic phase was passed through a hydrophobic fit. The solvent was removed in vacuo and the residue was used directly in the next step without any further purification. LCMS (Method 2): [MH+]=278 at 3.60 min.

Workup

customThe solvent was removed in vacuo
customThe mixture was partitioned between DCM (15 mL) and water (15 mL)
customthe layers were separated
customThe solvent was removed in vacuo
customthe residue was used directly in the next step without any further purification
customat 3.60 min.

Sources & evidence

ORD record: ord-ba4959fc871946ae8949319b0885d9c1
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199980B2

Reaction notes

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