Benzyl Bromide → 2-(Benzyloxy)-5-bromo-1,3-dimethylbenzene

HRID 1297764Notes

Reaction equation

HRID 1297764 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:4]([CH3:10])[CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 169194-Bromo-2,6-dimethylphenol

Product 1

HCID 229631332-(Benzyloxy)-5-bromo-1,3-dimethylbenzeneYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dissolve 4-bromo-2,6-dimethyl-phenol (20.1 g, 100 mmol) in DMF (250 mL) under nitrogen. Add cesium carbonate (48.9 g, 150 mmol) and benzyl bromide (13.1 mL, 110 mmol) and heat at 70° C. stirring mechanically for 6 h. Dilute with water (400 mL) and extract with 3/1 diethyl ether/hexanes (2×400 mL). Wash combined organics with brine (300 mL) and then dry (MgSO4), filter and concentrate in vacuo to give 28.67 g (99%) of the title compound as an oil which solidified on standing. 1H NMR(CDCl3): δ7.51-7.37 (m, 5H), 7.22 (s, 2H), 4.82 (s, 2H), 2.31 (s, 6H).

Workup

  1. extractionextract with 3/1 diethyl ether/hexanes (2×400 mL)
  2. washWash
  3. dry with materialdry (MgSO4)
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-20123a49cc774878ada52ec08ac7fe32
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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