Toluene → HCID 44544164, compound

HRID 658510Notes

Reaction equation

HRID 658510 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][C:10]=2[F:18])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:19](Br)[CH2:20]Br.C1(C)C=CC=CC=1.[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:16]#[N:17])[CH2:20][CH2:19]3)=[CH:11][C:10]=2[F:18])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 1140TolueneHCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 66916707(3',4'-Dichloro-2-fluoro-biphenyl-4-yl)-acetonitrile

Product 1

HCID 44544164HCID 44544164, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

3′,4′-dichloro-2-fluoro-4-cyanomethyl-biphenyl (9.0 g, 0.032 mol), 1,2-dibromomethane (9.0 g, 0.048 mol), 1.2 tetrabutylammonium chloride (1.2 g, 0.043 mol), toluene (60 ml), and water (9 ml) were loaded in a reactor. Sodium hydroxide 30% aq. (60 g, 0.45 mol) was added drop-wise over 30 minutes at 20 to 25° C. and the reaction mixture was stirred for 6 hours. The organic phase was separated, washed with water (12 ml), with hydrogen chloride 3 M aq. (36 ml) and finally with water (12 ml). The solution was concentrated, then n-heptane (18 ml) was added at 80° C. The solution was cooled to 0 to 5° C. and stirred for 30 minutes. The product crystallized from solution, it was filtered, washed with cold n-heptane (5 ml) and dried at 40° C. under vacuum. The compound 1-(3′,4′-dichloro-2-fluoro[1,1′-biphenyl]-4-yl)-cyclopropanenitrile was obtained as a yellow powder (6.4 g, 65% yield).

Workup

  1. customThe organic phase was separated
  2. washwashed with water (12 ml), with hydrogen chloride 3 M aq. (36 ml) and finally with water (12 ml)
  3. concentrationThe solution was concentrated
  4. additionn-heptane (18 ml) was added at 80° C
  5. stirringstirred for 30 minutes
  6. customThe product crystallized from solution, it
  7. filtrationwas filtered
  8. washwashed with cold n-heptane (5 ml)
  9. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-37d07be441c9406fbe603758159e5e62
Source dataset
uspto-grants-2011_12
Patent number
US08076505B2

Reaction notes

Loading…