Trichloroacetonitrile → 4-Bromo-2-chloro-5-fluorobenzyl 2,2,2-trichloroacetimidate

HRID 1427829Notes

Reaction equation

HRID 1427829 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][OH:10])=[C:4]([Cl:11])[CH:3]=1.N12CCCN=C1CCCCC2.[Cl:23][C:24]([Cl:28])([Cl:27])[C:25]#[N:26]>C(Cl)Cl>[Cl:23][C:24]([Cl:28])([Cl:27])[C:25](=[NH:26])[O:10][CH2:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([Br:1])=[CH:3][C:4]=1[Cl:11]

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67450751(4-Bromo-2-chloro-5-fluorophenyl)methanol

Product 1

HCID 867028534-Bromo-2-chloro-5-fluorobenzyl 2,2,2-trichloroacetimidateYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-bromo-2-chloro-5-fluorophenyl)methanol (3.95 g, 16.49 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.5 mL, 3.34 mmol) in methylene chloride (30 mL) was added trichloroacetonitrile (, 2.50 mL, 24.93 mmol) over 5 min at 0° C., stirring was continued for 4 h at 0° C. After concentrated in vacuo, the residue was purified by column chromatography eluting with 5% ethyl acetate in hexanes to give 4-bromo-2-chloro-5-fluorobenzyl 2,2,2-trichloroacetimidate as a colorless solid (5.80 g, 91%): δ 8.49 (s, 1H), 7.59 (d, J=6.3 Hz, 1H), 7.32 (d, J=9.0 Hz, 1H), 5.37 (s, 2H).

Workup

  1. concentrationAfter concentrated in vacuo
  2. customthe residue was purified by column chromatography
  3. washeluting with 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-453fe45170e24d2b92b44d91ffe2c6a6
Source dataset
uspto-grants-2015_01
Patent number
US08933236B2

Reaction notes

Loading…