1,2-Dibromoethane → Ethyl 3-(2-bromoethoxy)benzoate

HRID 2168219Notes

Reaction equation

HRID 2168219 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C([O-])([O-])=O.[K+].[K+].[Br:19][CH2:20][CH2:21]Br>C(#N)C>[Br:19][CH2:20][CH2:21][O:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 24522Ethyl 3-hydroxybenzoate

Product 1

HCID 54408639Ethyl 3-(2-bromoethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 3-hydroxybenzoate D45 (5 g) and K2CO3 (12.48 g, 90 mmol) in Acetonitrile (150 mL) stirred under nitrogen was added 1,2-dibromoethane (33.9 g, 181 mmol). The reaction mixture was stirred at 60° C. overnight. The reaction mixture was filtered, concentrated to give the crude as clear oil. The crude was purified to give the expected product D46 in 4.2 g, eluting with Petroleum oil/EtOAc=3/1. LCMS Retention time=1.76 mins, [M+H]+273 (5 min run)

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customto give the crude as clear oil
  4. customThe crude was purified

Sources & evidence

ORD record
ord-5fecbde5f70149079633436059ec7f6f
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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