Water → HCID 66750509, compound

HRID 643865Notes

Reaction equation

HRID 643865 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7](O)[CH:6]=2.[C:14](=[O:17])([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C=O)C>[CH2:20]([O:13][C:3]1[C:2]([Br:1])=[CH:11][C:10]2[C:5]([CH:4]=1)=[CH:6][C:7]([O:17][CH2:14][C:2]1[CH:3]=[CH:4][CH:5]=[CH:10][CH:11]=1)=[CH:8][CH:9]=2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14954841HCID 14954841, compound

Product 1

HCID 66750509HCID 66750509, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3-Bromonaphthalene-2,7-diol (1.40 g, 5.88 mmol) is dissolved in 20 mL of DMF. Potassium carbonate (2.44 g, 17.6 mmol) is added and the mixture is heated to 60° C. Benzyl bromide (2.10 mL, 17.64 mmol) is added and heating is continued for 5 h, after which time the reaction is poured into water and extracted with MTBE. The combined organics are dried and evaporated to afford 3,6-bis-benzyloxy-2-bromonaphthalene as a brown solid, which is of sufficient purity to take on to the next step.

Workup

  1. temperatureheating
  2. extractionextracted with MTBE
  3. customThe combined organics are dried
  4. customevaporated

Sources & evidence

ORD record
ord-9bc902bb8e1a4ee89f1291322d11b0f2
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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