Benzyl Bromide → HCID 68431966, compound

HRID 2244001Notes

Reaction equation

HRID 2244001 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:9][C:10]1[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][C:11]=1O.[C:18](=[O:21])([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([O:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([O:21][CH2:18][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]=1[I:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 6168332-iodobenzene-1,3-diol

Product 1

HCID 68431966HCID 68431966, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add benzyl bromide (7.97 g, 46.6 mmol) to a solution of 2-iodo-benzene-1,3-diol (5.00 g, 21.2 mmol) and cesium carbonate (15.2 g, 46.6 mmol) in dimethylformamide (200 mL) and stir. After 18 hours, concentrate under reduced pressure. Add water (500 mL) and stir. After 1 hour, filter the resulting precipitate washing with water and hexanes to yield the title compound as an off-white solid (6.30 g, 71%): 1H NMR (CDCl3) δ 5.18 (s, 4H), 6.55 (d, 2H), 7.19 (t, 1H), 7.29-7.53 (m, 10H).

Workup

  1. concentrationconcentrate under reduced pressure
  2. stirringAdd water (500 mL) and stir
  3. waitAfter 1 hour
  4. filtrationfilter the resulting precipitate
  5. washwashing with water and hexanes

Sources & evidence

ORD record
ord-d371244c36ce407f83e0abf974c2e29a
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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