Benzyl Bromide → HCID 10691343, compound

HRID 322919Notes

Reaction equation

HRID 322919 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[CH2:23]([O:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10780025HCID 10780025, compound

Product 1

HCID 10691343HCID 10691343, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of methyl 2-hydroxy-4-(4-chlorobenzyloxy)benzoate (5.2 g) in dry dimethylformamide (DMF) (50 mL) is treated with NaH (60% dispersion, 0.71 g) and stirred at 25° C. for 20 minutes. Benzyl bromide (2.12 mL) is added and the solution heated at 60° C. for 2 hours. The solution is evaporated. The residue is dissolved in ethyl acetate, washed with water, dried, and evaporated. The residue is recrystallized from ethyl acetate to yield methyl 2-benzyloxy-4-(4-chlorobenzyloxy)benzoate as colourless crystals (5.1 g, 75%), m.p. 99-101° C. 1H NMR (DMSO) 3.8(3H,s),5.18 (2H,s), 5.21(2H,s), 6.7(1H,d), 6.85(1H,s), 7.3-7.5(9H,m), 7.75(1H,d).

Workup

  1. temperaturethe solution heated at 60° C. for 2 hours
  2. customThe solution is evaporated
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e27084bacf884e3ea94af67978398771
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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