Benzyl Bromide → HCID 59570055, compound

HRID 2071147Notes

Reaction equation

HRID 2071147 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOCC>[CH2:1]([O:9][C:10]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10889156dimethyl 2-hydroxyisophthalate

Product 1

HCID 59570055HCID 59570055, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (0.34 ml, 0.49 g, 2.89 mmol, 1.5 eq) was added to a stirred suspension of dimethyl 2-hydroxyisophthalate (0.4045 g, 1.92 mmol, 1 eq) and K2CO3 (0.5317 g, 3.85 mmol, 2 eq) in anhydrous DMF (2 ml) under Ar. After 48 h the reaction was diluted with Et2O. The mixture was washed with water (×4), brine (×1), and dried over Na2SO4. The inorganics were filtered off and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.5207 g (1.73 mmol, 90% yield) of dimethyl 2-(benzyloxy)isophthalate.

Workup

  1. washThe mixture was washed with water (×4), brine (×1)
  2. dry with materialdried over Na2SO4
  3. filtrationThe inorganics were filtered off
  4. customthe solvent was removed in vacuo
  5. customPurification via flash chromatography

Sources & evidence

ORD record
ord-72f5761a0a054560a2a9ec3f2ed0afe2
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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