1-(2-Bromoethyl)-4-chlorobenzene → HCID 19970179, compound

HRID 974971Notes

Reaction equation

HRID 974971 reaction equation
[C:1]([C:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)#[N:2].[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29][Br:30])=[CH:26][CH:25]=1>>[Br-:30].[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29][N+:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][C:3]([C:1]#[N:2])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 230291-(2-Bromoethyl)-4-chlorobenzeneHCID 19970204HCID 19970204, compound

Product 1

HCID 19970179HCID 19970179, compoundYield 14.7%

Conditions

Temperature
115 °C

Procedure

A mixture of 2-(2-cyano-2,2-diphenylethyl)pyridine (1.70 g, 6 mmol) (see Preparation 5) and 4-chlorophenethyl bromide (1.10 g, 5 mmol) was heated at 115° C. for 26 hours, allowed to cool to room temperature and triturated with ethanol:ether=1:2 (15 ml). The resulting solid was collected, washed with ether, dried and recrystallised first from water and then from ether/2-propanol to give the title compound (0.37 g, 14%) as colourless crystals, m.p. 210°-211° C.

Workup

  1. temperatureto cool to room temperature
  2. customtriturated with ethanol
  3. customThe resulting solid was collected
  4. washwashed with ether
  5. customdried
  6. customrecrystallised first from water

Sources & evidence

ORD record
ord-48341e4636a848b89faee4a876b220a4
Source dataset
uspto-grants-1997_03
Patent number
US05607950

Reaction notes

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