Benzyl Bromide → Benzyl 2-benzyloxy-4-iodobenzoate

HRID 322936Notes

Reaction equation

HRID 322936 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([OH:13])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[CH2:14]([O:13][C:6]1[CH:5]=[C:4]([I:3])[CH:12]=[CH:11][C:7]=1[C:8]([O:10][CH2:8][C:7]1[CH:11]=[CH:12][CH:4]=[CH:5][CH:6]=1)=[O:9])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 728742-Hydroxy-4-iodobenzoic acid

Product 1

HCID 10599389Benzyl 2-benzyloxy-4-iodobenzoateYield 109.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (4.7 g, 60% dispersion in mineral oil) is added portionwise over 15 minutes to a solution of 4-iodosalicylic acid (15.4 g) in dry dimethylformamide (150 mL). After stirring for 40 minutes benzyl bromide (19.9 g) is added and the mixture heated at 60° C. for 1.5 hours. The reaction mixture is evaporated and the residue partitioned between chloroform and water. The organic phase is dried over magnesium sulphate, evaporated and the residue triturated with ether to give benzyl 2-benzyloxy-4-iodobenzoate (14.2 g) as a cream coloured solid.

Workup

  1. additionis added
  2. customThe reaction mixture is evaporated
  3. customthe residue partitioned between chloroform and water
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customevaporated
  6. customthe residue triturated with ether

Sources & evidence

ORD record
ord-4c0712885e76458ebae96595ab713b5e
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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