3-Bromophenol → HCID 19744768, compound

HRID 2254474Notes

Reaction equation

HRID 2254474 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].C1([O-])C=CC=CC=1.[Br:18][C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1.[H-].[Na+]>CN(C)C=O.O1CCCC1>[Br:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[O:25][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7]

Participants

7

Reactant 4

HCID 115633-BromophenolHCID 24758Sodium hydrideHCID 119047PhenolateHCID 71278253-(Bromomethyl)benzaldehyde

Product 1

HCID 19744768HCID 19744768, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.4 g of 3-bromomethylbenzaldehyde was dissolved in 3 ml of dimethylformamide, and the solution was added to 5 ml of a tetrahydrofuran solution of phenolate, prepared from 1.5 g of 3-bromophenol and 0.36 g of 60% oily sodium hydride. The mixture was stirred for 2 hours at room temperature. The solvent was evaporated, and water and ethyl acetate were added to the residue to extract it. The extract was worked up in a customary manner to give crude 3-(3-bromophenoxymethyl)benzaldehyde. When the same reaction as in Referential Example 12 was performed using 440 mg of the resulting aldehyde compound, 747 mg of tributyl(3-thienyl)stannane and 10 mg of tetrakis(triphenylphosphine)palladium, 341 mg (yield 77%) of 3-[3-(3-thienyl)phenoxymethyl)benzaldehyde was obtained.

Workup

  1. customThe solvent was evaporated
  2. additionwater and ethyl acetate were added to the residue
  3. extractionto extract it

Sources & evidence

ORD record
ord-ba57e2fffba04689866def133feb9f1c
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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