Propargyl bromide → Benzenamine, 4-chloro-2-fluoro-5-(2-propynyloxy)-

HRID 263385Notes

Reaction equation

HRID 263385 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([OH:11])[C:6]([Cl:10])=[CH:7][C:8]=1[F:9].[CH2:12](Br)[C:13]#[CH:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:10][C:6]1[C:5]([O:11][CH2:14][C:13]#[CH:12])=[CH:4][C:3]([NH2:2])=[C:8]([F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 190373173-Amino-6-chloro-4-fluorophenol hydrochloride

Product 1

HCID 13272927Benzenamine, 4-chloro-2-fluoro-5-(2-propynyloxy)-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure of Example 1, Step A and employing 50.0 g (252.45 mmol) of 3-amino-6-chloro-4-fluorophenol hydrochloride, 80% propargyl bromide (60.07 g, 504.9 mmol), and potassium carbonate (69.8 g, 504.9 mmol) in acetonitrile (200 mL), the title compound was obtained as a yellow solid (16.2 g), m.p. 62°-64° C. IR (nujol, era-1), NH2 (3298.0), triple bond (2117.6). 1H NMR was consistent with the structure.

Sources & evidence

ORD record
ord-a32c0927db4b4ffa980dcbd2d4a5b16c
Source dataset
uspto-grants-1997_07
Patent number
US05643855

Reaction notes

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