Water → (4-Bromo-naphthalen-1-yl)-oxo-acetic acid methyl ester

HRID 2353544Notes

Reaction equation

HRID 2353544 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7](=[O:11])[C:8](Cl)=[O:9].[Br:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.O>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:11])[C:8]([C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([Br:12])=[CH:14][CH:15]=1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 70011-BromonaphthaleneHCID 79846Methyl chloroglyoxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 59379801(4-Bromo-naphthalen-1-yl)-oxo-acetic acid methyl esterYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of AlCl3 (3.20 g, 24 mmol) in 100 mL DCM at 0° C., methylchloroglyoxylate (2.2 mL, 24 mmol) was added. The resulting solution was stirred for 5 min., after which 1-bromo-naphthalene (5 g, 24 mmol) was added. After stirring for 2 hrs at room temperature, water was added and the phases were separated, after which the organic layer was washed with water and dried over MgSO4. The residue obtained after evaporation of the organic solvent was purified by column chromatography (0-30% EtOAc/Hex), to afford 2.6 g of the target compound. 1H NMR (CDCl3): 8.92 (1H, d, J=9.3 Hz, H-arom); 8.31 (1H, d, J=9.3 Hz, H-arom); 7.82 (1H, d, J=8.8 Hz, H-arom); 7.72 (1H, d, J=8.8 Hz, H-arom); 7.57-7.68 (2H, m, H-arom); 3.94 (3H, s, OMe).

Workup

  1. stirringAfter stirring for 2 hrs at room temperature
  2. customthe phases were separated
  3. washafter which the organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. customThe residue obtained
  6. customafter evaporation of the organic solvent
  7. customwas purified by column chromatography (0-30% EtOAc/Hex)

Sources & evidence

ORD record
ord-07d4ea47ecb14b25b4a0514eaa5dcb14
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

Loading…