Benzyl Bromide → 2-Benzyloxy-1-bromo-6-methoxy-naphthalene

HRID 445197Notes

Reaction equation

HRID 445197 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:14].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([O:14][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)[C:2]=1[Br:1])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 184287461-Bromo-6-methoxynaphthalen-2-ol

Product 1

HCID 117029082-Benzyloxy-1-bromo-6-methoxy-naphthaleneYield 37.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 1-bromo-6-methoxy-naphthalen-2-ol (66.7 g, 264 mmol), potassium carbonate (K2CO3, 40.0 g, 290 mmol) and benzyl bromide (49.6 g, 290 mmol) to DMF (800 mL). Stir the mixture at ambient temperature for 1 hour. Add water (400 mL) to precipitate the product. Collect the precipitate and wash the filter cake with heptane (3×125 mL) then dry to provide 2-benzyloxy-1-bromo-6-methoxy-naphthalene (83.7 g, 98.9 mmol).

Workup

  1. customAdd water (400 mL) to precipitate the product
  2. customCollect the precipitate
  3. washwash the filter cake with heptane (3×125 mL)
  4. customthen dry

Sources & evidence

ORD record
ord-ce72f5b9b1ff4692a1324da43746eb77
Source dataset
uspto-grants-2013_07
Patent number
US08476300B2

Reaction notes

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