Triethylamine → Methyl 3-(bromomethyl)benzoate

HRID 1684962Notes

Reaction equation

HRID 1684962 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].C(N(CC)CC)C.[C:19](=O)([O-])[OH:20].[Na+]>CO>[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([O:20][CH3:19])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 144710763-(Bromomethyl)benzoyl chloride

Product 1

HCID 517981Methyl 3-(bromomethyl)benzoateYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Bromomethylbenzoyl chloride (1.96 g, 10.37 mmol) was dissolved in methanol (20 ml), and triethylamine (1.5 ml) was added thereto. The mixture was stirred at room temperature for 1 hour. The mixture was poured into a saturated sodium hydrogencarbonate solution and was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give the captioned compound (1.90 g, 10.29 mmol, yield: 97%) as a colorless oil.

Workup

  1. extractionwas extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c825d55f32984ed39b8dd4a2c204e07c
Source dataset
uspto-grants-2012_04
Patent number
US08148371B2

Reaction notes

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