Triethylamine → 3-Chloro-2-(7-chloro-1,3-benzodioxol-5-yl)-4,4,4-trifluoro-but-2-enenitrile

HRID 705705Notes

Reaction equation

HRID 705705 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH:11]([C:14](=O)[C:15]([F:18])([F:17])[F:16])[C:12]#[N:13])[CH:3]=1.O=P(Cl)(Cl)[Cl:22].C(N(CC)CC)C>O>[Cl:22][C:14]([C:15]([F:18])([F:17])[F:16])=[C:11]([C:4]1[CH:3]=[C:2]([Cl:1])[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)[C:12]#[N:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 900100662-(7-Chloro-1,3-benzodioxol-5-yl)-4,4,4-trifluoro-3-oxo-butanenitrile

Product 1

HCID 1317336953-Chloro-2-(7-chloro-1,3-benzodioxol-5-yl)-4,4,4-trifluoro-but-2-enenitrileYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2-(7-chloro-1,3-benzodioxol-5-yl)-4,4,4-trifluoro-3-oxo-butanenitrile (23.9 g, 82 mmol) was treated with POCl3 (62.0 g, 0.41 mol) and then triethylamine (11.4 mL, 82 mmol) was added. The reaction mixture was heated for 3 h at 80-100° C. and then carefully poured into warm water. The product was then extracted ethyl acetate, washed with water and brine, dried, filtered and concentrated to give the title compound (20.2 g; 80%) and used for the next step directly.

Workup

  1. additioncarefully poured
  2. washextracted ethyl acetate, washed with water and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-590bf6263931476899f6d0f8873d9761
Source dataset
uspto-grants-2015_11
Patent number
US09174967B2

Reaction notes

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