Pyridine → 2-Bromoethyl-3-chlorobenzoate

HRID 731764Notes

Reaction equation

HRID 731764 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].N1C=CC=CC=1.[Br:17][CH2:18][CH2:19][OH:20]>ClCCl>[Br:17][CH2:18][CH2:19][O:20][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 108982-BromoethanolHCID 69252Benzoyl chloride, 3-chloro-

Product 1

HCID 214111272-Bromoethyl-3-chlorobenzoateYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chlorobenzoyl chloride (2) (0.21 g, 2.8 mmol) and pyridine (0.46 mL, 5.7 mmol) in anhydrous dichloromethane (10 mL) at room temperature was (dropwise) added 2-bromoethanol (1) (0.23 mL, 3.1 mmol). The reaction mixture was stirred for 2 h at room temperature and quenched with 1N HCl. The organic phase was washed with saturated aqueous solution of NaHCO3, brine and then dried over anhydrous MgSO4. The crude product was purified by silica gel chromatography to give 2-bromoethyl 3-chlorobenzoate (3) as colorless oil (0.64 g). 1H NMR (CDCl3): δ 8.04 (t, J=1.8 Hz, 1H), 7.98-7.93 (m, 1H), 7.58-7.52 (m, 1H), 7.40 (t, J=8.4 Hz, 1H), 4.63 (t, J=6.0 Hz, 2H), 3.64 (t, J=6.0 Hz, 2H)

Workup

  1. customat room temperature
  2. customquenched with 1N HCl
  3. washThe organic phase was washed with saturated aqueous solution of NaHCO3, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7fe229187ef4457d9c258192bf76d507
Source dataset
uspto-grants-2009_09
Patent number
US07585883B2

Reaction notes

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