1,2-Dichloroethane → Methyl 3-bromo-5-formylbenzoate

HRID 1441968Notes

Reaction equation

HRID 1441968 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH:11]=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].CO.[CH2:15](Cl)CCl>C(#N)C.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH:11]=[O:12])[CH:10]=1)[C:5]([O:7][CH3:15])=[O:6]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 887MethanolHCID 223207963-Bromo-5-formylbenzoic acid

Product 1

HCID 11436457Methyl 3-bromo-5-formylbenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
-10 °C

Procedure

6.2 g (27.1 mmol) of 3-bromo-5-formylbenzoic acid (J. Org. Chem., 2002, 67, 3548-3554) are dissolved in 110 ml of acetonitrile under argon. 330 mg (2.7 mmol) of 4-dimethylaminopyridine and 1.73 ml (54.2 mmol) of methanol are added thereto. The mixture is cooled to −10° C., and 6.23 g (32.5 mmol) of EDC are added. The mixture is slowly allowed to reach RT and is then stirred for 20 h. The solvent is then evaporated in vacuo, and the residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate (6:1)).

Workup

  1. customto reach RT
  2. customThe solvent is then evaporated in vacuo
  3. customthe residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate (6:1))

Sources & evidence

ORD record
ord-3d71b3a9294c430b9a896a4762664c1a
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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