Thiophosgene → 2-Chloro-4-fluoro-1-isothiocyanatobenzene

HRID 1898300Notes

Reaction equation

[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10](Cl)(Cl)=[S:11].C(N(C(C)C)C(C)C)C>>[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[N:4]=[C:10]=[S:11]

Participants

Reactant 3

HCID 10040Thiophosgene

HCID 75013Benzenamine, 2-chloro-4-fluoro-

HCID 81531Diisopropylethylamine

Product 1

HCID 27575812-Chloro-4-fluoro-1-isothiocyanatobenzeneYield 46.6%

Procedure

The title compound was prepared following the procedure described for intermediate-2 using 2-chloro-4-fluoro aniline (5.0 g, 34.48 mmol), thiophosgene (3.95 g, 34.34 mmol), N-ethyl di-isopropyl amine (8.80 g, 68.00 mmol) to afford 3.0 g of the desired product.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-73ee302f906f4566aceadc7713bfbc74
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519149B2

Reaction notes

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