4-Bromo-1,2-dichlorobenzene → 1-(3,4-Dichlorophenyl)-2-methoxyethanone

HRID 2279501

Reaction equation

HRID 2279501 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([Cl:9])[CH:3]=1.[Li]CCCC.CON(C)[C:18](=[O:22])[CH2:19][O:20][CH3:21]>CCOCC>[Cl:9][C:4]1[CH:3]=[C:2]([C:18](=[O:22])[CH2:19][O:20][CH3:21])[CH:7]=[CH:6][C:5]=1[Cl:8]

Participants

5

Reactant 3

HCID 290134-Bromo-1,2-dichlorobenzeneHCID 14872187N,2-dimethoxy-N-methylacetamideHCID 178418339Butyllithium

Product 1

HCID 202556411-(3,4-Dichlorophenyl)-2-methoxyethanoneYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4-bromo-1,2-dichlorobenzene (2.04 g, 9.01 mmol) and ether (5 mL) cooled to −78° C. was added as a steady stream n-BuLi (3.61 ml, 9.01 mmol) and the reaction was stirred for 10 min then cannulated into a solution of N,2-dimethoxy-N-methylacetamide (1.0 g, 7.51 mmol) and ether (10 mL) which was stirred for an additional 20 min. The reaction was quenched with water and extracted with EtOAc. The organic fractions were dried, filtered and concentrated. The crude product which was purified by SiO2 chromatography eluting with hexane/EtOAc (9:1) to afford 1.30 g (79.0%) of 1-(3,4-dichlorophenyl)-2-methoxyethanone as a white solid (192).

Workup

  1. stirringwas stirred for an additional 20 min
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. customThe organic fractions were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product which was purified by SiO2 chromatography
  8. washeluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-659f627637a14cbf883628fb6637c826
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Linked notes

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