Water → 3-Benzyloxy-4,5-dimethoxybromobenzene

HRID 588334Notes

Reaction equation

HRID 588334 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([O:13][CH3:14])[C:7]([O:11][CH3:12])=[C:8]([OH:10])[CH:9]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[CH2:15]([O:10][C:8]1[CH:9]=[C:4]([Br:3])[CH:5]=[C:6]([O:13][CH3:14])[C:7]=1[O:11][CH3:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 250528855-Bromo-2,3-dimethoxyphenol

Product 1

HCID 666027283-Benzyloxy-4,5-dimethoxybromobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% in mineral oil, 300 mg) was added in 3 equal portions to a cooled 0° C. solution of 5-bromo-2,3-dimethoxyphenol (1.16 g) in DMF (10 mL) After 20 minutes, benzyl bromide (0.9 ml) was added, and the reaction mixture was allowed to warm to room temperature and stir overnight. The reaction mixture was then poured into 100 mL of water and extracted with ethyl acetate (4×50 mL). The combined organic layer was then washed with water (4×75 mL) followed by brine (75 mL) and then dried over sodium sulfate and concentrated under vacuum. Chromatography on silica with 5% ethyl acetate/hexane provided 3-benzyloxy-4,5-dimethoxybromobenzene as a colorless oil (1.4 g). 1H NMR (400 MHz) (CDCl3) δ 3.87 (s, 6H), 5.12 (s, 2H), 6.75 (s, 1H), 6.80 (s, 1H), 7.34-7.47 (m, 5H).

Workup

  1. extractionextracted with ethyl acetate (4×50 mL)
  2. washThe combined organic layer was then washed with water (4×75 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-998efab353224f46937bb6ea1d592481
Source dataset
uspto-grants-2016_01
Patent number
US09227966B2

Reaction notes

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