Dibromomethane → HCID 15036438, compound

HRID 1534111Notes

Reaction equation

HRID 1534111 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH:12]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])[C:13]#[N:14])=[CH:6][CH:5]=1.C(Br)Br.[NH:26]1[CH:30]=CN=[N:27]1.C[N:32]([CH:34]=O)[CH3:33]>>[Cl:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([F:21])[C:15]=1[C:12]([CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=1)([CH2:30][N:26]1[CH:34]=[N:32][CH:33]=[N:27]1)[C:13]#[N:14]

Participants

6

Reactant 5

HCID 3024DibromomethaneHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 15036436HCID 15036436, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 15036438HCID 15036438, compound

Procedure

A 3 neck 200 ml round bottom flask was charged with 2.4 gms of 60% NaH (0.048 mole, 1.2 eq.), washed twice with 25 ml of hexanes, in 40 ml of DMF. At room temperature 12.28 gms (0.04 mole, 1.0 eq.) of alpha-[2-(4-chlorophenyl)ethyl]-2-chloro-6-fluorophenylacetonitrile was added dropwise over 0.5 hour in 30 ml of DMF. Then 10.43 gms of CH2Br2 (0.60 mole, 1.5 eq.) in 20 ml of DMF was added dropwise and the reaction was stirred at room temperature for 0.5 hour after which gas liquid chromatography indicated that the reaction was complete. The reaction was quenched after 1 hour by adding 20 ml of water and 200 ml of ether which was separated. After washing with water, drying and concentrating 14.84 gms (92.9% yield) resulted which was used directly in the triazole coupling.

Workup

  1. washwashed twice with 25 ml of hexanes, in 40 ml of DMF
  2. customThe reaction was quenched after 1 hour
  3. additionby adding 20 ml of water and 200 ml of ether which
  4. customwas separated
  5. washAfter washing with water
  6. customdrying
  7. concentrationconcentrating 14.84 gms (92.9% yield)
  8. customresulted which

Sources & evidence

ORD record
ord-eb3e56faad994f92951d054399940d70
Source dataset
uspto-grants-1992_02
Patent number
US05087635

Reaction notes

Loading…