Thiophosgene → 4-Bromo-2-fluorophenylisothiocyanate

HRID 1177441Notes

Reaction equation

HRID 1177441 reaction equation
[C:1](Cl)(Cl)=[S:2].C(=O)([O-])[O-].[Na+].[Na+].[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([F:19])[CH:13]=1>C(Cl)(Cl)Cl>[Br:11][C:12]1[CH:18]=[CH:17][C:15]([N:16]=[C:1]=[S:2])=[C:14]([F:19])[CH:13]=1

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 10340Sodium CarbonateHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 27570034-Bromo-2-fluorophenylisothiocyanate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thiophosgene (22 mL, 289 mmol) was added to a suspension of sodium carbonate (61.0 g, 579 mmol) and 4-bromo-2-fluoroaniline (50.0 g, 263 mmol) in CHCl3 (1 L). The reaction mixture was stirred overnight at RT, the inorganic salts were filtered off, and the filtrate was concentrated to give 4-bromo-2-fluoro-1-isothio-cyanatobenzene as a tan solid which was converted to 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-bromobenzo[d]thiazole as described in Reference A above.

Workup

  1. filtrationthe inorganic salts were filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0b11cc47812041f692b9405a969311b2
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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