Methyl iodide → HCID 59394935, compound

HRID 471959Notes

Reaction equation

HRID 471959 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([OH:11])=[C:4]([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:3]=1.[C:17]([O-])([O-])=O.[Cs+].[Cs+].IC>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:5]([O:11][CH3:17])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 59395034HCID 59395034, compound

Product 1

HCID 59394935HCID 59394935, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-bromo-2-cyclopentyl-5-nitro-phenol (310 mg, 1.08 mmol) and Cs2CO3 (529 mg, 1.62 mmol) in DMF (2.0 mL) was added iodomethane (769 mg, 337 μL, 5.42 mmol) dropwise. The reaction was stirred at 50° C. under inert atmosphere for 16 h. The reaction was quenched with water and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated. Purification by silica gel chromatography (0-20% ethyl acetate/hexane) provided 1-bromo-5-cyclopentyl-4-methoxy-2-nitrobenzene as a light yellow oil (288 mg, 89% yield). 1H NMR (400.0 MHz, DMSO-d6) 7.65 (d, J=6.6 Hz, 2H), 3.87 (s, 3H), 3.29-3.21 (m, 1H), 1.99-1.91 (m, 3H), 1.81-1.50 (m, 5H).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (0-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-54fd565f73684652ac612bbd86801d2f
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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