Benzyl Bromide → Methyl 4-benzyloxy-3-tert-butyl-5-iodobenzoate

HRID 2377197Notes

Reaction equation

HRID 2377197 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([I:16])[C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([O:15][C:14]1[C:13]([I:16])=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 12084815Methyl 3-t-butyl-4-hydroxy-5-iodobenzoate

Product 1

HCID 12084816Methyl 4-benzyloxy-3-tert-butyl-5-iodobenzoateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24.1 g (72 mmol) of methyl 3-tert-butyl-4-hydroxy-5-iodobenzoate are dissolved in 200 mL of dimethylformamide. 3.47 g (86 mmol) of 60% sodium hydride are added slowly and the reaction medium is stirred for 1 hour. 9.4 mL (79 mmol) of benzyl bromide are then added and the medium is stirred at room temperature for 2 hours, and is then hydrolysed and extracted with ethyl ether. The organic phase is washed 3 times with water and then concentrated under reduced pressure. The residue is purified by chromatography (eluent: 98 heptane/2 ethyl acetate). A yellow oil is obtained (m=24.3 g; yield=80%).

Workup

  1. stirringthe medium is stirred at room temperature for 2 hours
  2. extractionhydrolysed and extracted with ethyl ether
  3. washThe organic phase is washed 3 times with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography (eluent: 98 heptane/2 ethyl acetate)
  6. customA yellow oil is obtained (m=24.3 g; yield=80%)

Sources & evidence

ORD record
ord-b74b099914ac49539d1ba15387f66d1b
Source dataset
uspto-grants-2008_12
Patent number
US07468457B2

Reaction notes

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