Sodium Acetate → 8-bromo-2-methoxy-6H-dibenzo[c,h]chromene

HRID 1751527Notes

Reaction equation

HRID 1751527 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:21]=1)[CH2:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.C([O-])(=O)C.[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]3[C:9](=[C:18]4[CH:17]=[CH:16][C:15]([O:19][CH3:20])=[CH:14][C:13]4=[CH:12][CH:11]=3)[O:8][CH2:7][C:6]=2[CH:21]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 696729081-(5-Bromo-2-iodobenzyloxy)-6-methoxynaphthalene

Product 1

HCID 596108178-bromo-2-methoxy-6H-dibenzo[c,h]chromeneYield 35.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-(5-bromo-2-iodobenzyloxy)-6-methoxynaphthalene (5.0 g, 10.7 mmol) and sodium acetate (2.64 g, 32.1 mmol) in dimethylformamide (100 mL) was degassed with a stream of argon for 15 minutes. PdCl2(PPh3)2 was added and the reaction was heated to 110° C. After 16 hours the reaction was diluted with ethyl acetate, washed with water and brine, dried (Na2SO4) and concentrated. The resulting residue was purified by flash column chromatography to yield 8-bromo-2-methoxy-6H-dibenzo[c,h]chromene (1.29 g, 35%).

Workup

  1. customwas degassed with a stream of argon for 15 minutes
  2. additionPdCl2(PPh3)2 was added
  3. additionAfter 16 hours the reaction was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-13c99de87d734168b8c9ace838ffe338
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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