Water → Benzyl 2-bromo-3-methylphenethyl ether

HRID 427518Notes

Reaction equation

HRID 427518 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11][CH2:12][OH:13].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>O1CCCC1>[Br:3][C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 226725712-(2-Bromo-3-methylphenyl)ethan-1-ol

Product 1

HCID 18357451Benzyl 2-bromo-3-methylphenethyl etherYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (50% in oil) (1.7 g, 0.036 mol) was suspended in dry tetrahydrofuran (75 ml) in argon atmosphere. 2-(2-bromo-3-methylphenyl)-1-ethanol (7.0 g, 0.033 mol) solved in tetrahydrofuran (25 ml) was added dropwise during 30 min at room temperature. Benzyl bromide (6.2 g, 0.036 mol) was added and the reaction mixture was stirred at room temperature over night. Water (1.0 ml) was added carefully and the solvent was evaporated under reduced pressure. The residue was partitioned between water and diethyl ether and the water layer was extracted twice with diethyl ether. The ether extracts were combined, washed twice with water, and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using heptane:methylene chloride (7:3) as eluent gave 7.5 g (74.3%) of the title compound.

Workup

  1. additionwas added dropwise during 30 min at room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was partitioned between water and diethyl ether
  4. extractionthe water layer was extracted twice with diethyl ether
  5. washwashed twice with water
  6. customevaporated under reduced pressure
  7. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-95eaf920e9ec496eb29ff710dd7a8e4a
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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