Benzyl Bromide → Benzyl 4-bromo-3-methoxybenzoate

HRID 1908120Notes

Reaction equation

HRID 1908120 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:7])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 162158674-Bromo-3-methoxybenzoic acid

Product 1

HCID 58551480Benzyl 4-bromo-3-methoxybenzoateYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-3-methoxy-benzoic acid (1.50 g, 6.49 mmol), K2CO3 (2.69 g, 19.5 mmol), and DMF (10 mL) were combined and the mixture was allowed to stir for 10 minutes. Bromomethylbenzene (849 μL, 7.14 mmol) was added dropwise and the mixture was allowed to stir at rt for 1 h. The reaction mixture was quenched with brine and was extracted with EtOAc (3×). The organic layers were dried over sodium sulfate, filter and concentrated. The residue was purified using silica gel chromatography (5%-70% EtOAc in hexanes) to provide benzyl 4-bromo-3-methoxybenzoate (91%). ESI-MS m/z calc 320.0. found 321.0/323.0 (M+1)+. Retention time: 3.24 minutes (4 min run).

Workup

  1. stirringto stir at rt for 1 h
  2. customThe reaction mixture was quenched with brine
  3. extractionwas extracted with EtOAc (3×)
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-97d67d7a72814f23b0eeb2a3da560ad3
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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