Benzyl Bromide → HCID 11448276, compound

HRID 1912508Notes

Reaction equation

HRID 1912508 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[OH:1])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 287064Methyl 3,4-Dihydroxybenzoate

Product 1

HCID 11448276HCID 11448276, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of methyl 3,4-dihydroxybenzoate (10.0 g, 59.4 mmol) in acetone (400 mL) was added potassium carbonate (8.21 g, 59.5 mmol). The mixture was stirred at room temperature (rt) for 30 minutes (min). To the resulting mixture was added benzyl bromide (7 mL, 59.4 mmol) in acetone (200 mL) dropwise over 2 hours (h) and stirring was continued for 48 h. Acetone was removed under vacuum and the resulting residue was partitioned between water (100 mL) and ethyl acetate (3×25 mL). The organic layer was dried over NaSO4, concentrated under vacuum and the resulting crude material purified via column chromatography to afford the product 30 (8.00 g, 52%). 1H NMR (300 MHz, CDCl3): δ 7.70 (m, 2H), 7.50 (m, 5H), 6.95 (m, 1H), 5.70 (s, 1H), 5.10 (s, 2H), 3.93 (s, 3H). MS (M+H): 259.

Workup

  1. stirringstirring
  2. waitwas continued for 48 h
  3. customAcetone was removed under vacuum
  4. customthe resulting residue was partitioned between water (100 mL) and ethyl acetate (3×25 mL)
  5. dry with materialThe organic layer was dried over NaSO4
  6. concentrationconcentrated under vacuum
  7. customthe resulting crude material purified via column chromatography

Sources & evidence

ORD record
ord-41daa72bcdae4a64a41a9ded71c652ce
Source dataset
uspto-grants-2013_12
Patent number
US08609673B2

Reaction notes

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