Carbon tetrabromide → HCID 58258448, compound

HRID 514592Notes

Reaction equation

HRID 514592 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[Br:16][C:17](Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[C:8]([CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:7]=[CH:6][C:3]=1[CH:4]=[C:17]([Br:18])[Br:16]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 582584922-Chloro-4-(1-pyrrolidinylmethyl)benzaldehyde

Product 1

HCID 58258448HCID 58258448, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 2-chloro-4-(1-pyrrolidinylmethyl)-benzaldehyde (prepared according to the teachings in WO2008/148868) (10.0 g, 44.70 mmol) and tetrabromomethane (22.2 g, 67.05 mmol) in DCM (300 ml) was stirred at 0° C. A solution of triphenylphosphine (35.2 g, 134.10 mmol) in DCM (500 ml) was added. The mixture was stiffed for 30 min at 0° C. The mixture was concentrated in vacuo. The residue was taken up into CHCl3, and the precipitate was filtered off. The filtrate was concentrated in vacuo. The residue (crude 1-[[3-chloro-4-(2,2-dibromoethenyl)phenyl]methyl]-pyrrolidine) was used as such in the next reaction step.

Workup

  1. customprepared
  2. concentrationThe mixture was concentrated in vacuo
  3. filtrationthe precipitate was filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. customsuch in the next reaction step

Sources & evidence

ORD record
ord-6a52decb9a9b4d1c8b7334df3fa6f46d
Source dataset
uspto-grants-2015_08
Patent number
US09107946B2

Reaction notes

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