Dimethylformamide → 3-Bromo-1-chloro-5-(1-chloroethyl)-4-methoxy-2-methylbenzene

HRID 1499831Notes

Reaction equation

HRID 1499831 reaction equation
N1C(Cl)=NC(Cl)=NC=1[Cl:3].CN(C)C=O.[Br:15][C:16]1[C:17]([O:27][CH3:28])=[C:18]([CH:24](O)[CH3:25])[CH:19]=[C:20]([Cl:23])[C:21]=1[CH3:22]>C(Cl)Cl>[Br:15][C:16]1[C:21]([CH3:22])=[C:20]([Cl:23])[CH:19]=[C:18]([CH:24]([Cl:3])[CH3:25])[C:17]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7954Cyanuric chlorideHCID 866668161-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethanol

Product 1

HCID 866776443-Bromo-1-chloro-5-(1-chloroethyl)-4-methoxy-2-methylbenzeneYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of cyanuric chloride (1.7 g, 9.2 mmol) and N,N-dimethylformamide (710 μL, 9.2 mmol) was stirred at room temperature for 10 minutes and then a solution of 1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanol (from Example 16, Step 1) (1.72 g, 6.15 mmol) in methylene chloride (34 mL) was added and the reaction was stirred at room temperature overnight. The mixture was diluted with methylene chloride, washed with sat. NaHCO3, water, brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with 0 to 10% EtOAc in hexanes, to give the desired product (1.01 g, 60%).

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. washwashed with sat. NaHCO3, water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with 0 to 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-0eaebfa9534b4e50865af665a8bae73d
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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