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

HRID 469301Notes

Reaction equation

HRID 469301 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[OH:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:18][C:11]1[C:10]([CH3:9])=[CH:15][C:14]([Br:16])=[CH:13][C:12]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 169194-Bromo-2,6-dimethylphenol

Product 1

HCID 229631332-(Benzyloxy)-5-bromo-1,3-dimethylbenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

11.7 mL (96.5 mmol) benzylbromide were added dropwise to 20 g (96.5 mmol) 2,6-dimethyl-4-bromophenol and 16.5 g (118 mmol) potassium carbonate in 300 mL acetone and stirred overnight at RT. The precipitate formed was suction filtered, washed with acetone and the filtrate was evaporated down. The residue was dissolved in DCM, filtered through Alox and washed with DCM. The filtrate was evaporated down.

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. washwashed with acetone
  4. customthe filtrate was evaporated down
  5. dissolutionThe residue was dissolved in DCM
  6. filtrationfiltered through Alox
  7. washwashed with DCM
  8. customThe filtrate was evaporated down

Sources & evidence

ORD record
ord-cfa2eed5035345cca13736a15a3ded78
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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