Triethylamine → (3-Fluoro-4-isocyanato-phenoxy)-acetic acid methyl ester

HRID 1690557Notes

Reaction equation

HRID 1690557 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([F:14])[CH:8]=1.Cl[C:17](Cl)([O:19]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(CC)CC>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]=[C:17]=[O:19])=[C:9]([F:14])[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 66905560Methyl 2-[(4-amino-3-fluorophenyl)oxy]acetate hydrochloride

Product 1

HCID 86640266(3-Fluoro-4-isocyanato-phenoxy)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedure described in example 9.1, (4-amino-3-fluoro-phenoxy)-acetic acid methyl ester hydrochloride (Kori, Masakuni; Mild, Takashi; Nishimoto, Tomoyuki; Tozawa, Ryuichi. PCT Int. Appl. (2001), WO 2001098282 A1) was reacted with triphosgene in the presence of Et3N (3.5 eq.) in CH2Cl2 under reflux conditions for 14 h to give the title compound as brown solid. MS: m/e=243.1 [M+NH4+].

Sources & evidence

ORD record
ord-cb9fa308671943599fc3826a20d81f8f
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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