Triethylamine → 3-Bromo-2-chloro-6-fluorobenzonitrile

HRID 1508171Notes

Reaction equation

HRID 1508171 reaction equation
[Br:1][C:2]1[C:3]([Cl:12])=[C:4]([C:8]([F:11])=[CH:9][CH:10]=1)[C:5]([NH2:7])=O.CCN(CC)CC.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:12])=[C:4]([C:8]([F:11])=[CH:9][CH:10]=1)[C:5]#[N:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 712395033-Bromo-2-chloro-6-fluorobenzamide

Product 1

HCID 712393913-Bromo-2-chloro-6-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-2-chloro-6-fluorobenzamide (3.56 mmol) in 50 mL DCM were added 1.5 mL Et3N followed by trifluoromethanesulfonic acid anhydride (7.11 mmol) at 0° C. The ice bath was removed and the reaction mixture was stirred at RT. After 30 min, water was added and the mixture was extracted with DCM (3×). The combined organic layers were dried over MgSO4 and concentrated in vacuo to obtain the desired compound as brown solid.

Workup

  1. customThe ice bath was removed
  2. additionwater was added
  3. extractionthe mixture was extracted with DCM (3×)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0417eee7762a4333be31dc3b00dc285b
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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