Water → 6-bromo-3-(4-methylphenyl)-2H-1-benzopyran

HRID 1169351Notes

Reaction equation

HRID 1169351 reaction equation
[Br-].[Br:2][C:3]1[CH:4]=[CH:5][C:6]([O:29][CH2:30][C:31]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)=O)=[C:7]([CH:28]=1)[CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[O-]CC.[Na+].O>C(O)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[O:29][CH2:30][C:31]([C:33]3[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=3)=[CH:8][C:7]=2[CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 86759182[5-Bromo-2-[2-(4-methylphenyl)-2-oxoethoxy]benzyl](triphenyl)phosphonium bromide

Product 1

HCID 229901326-bromo-3-(4-methylphenyl)-2H-1-benzopyranYield 85.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Into a suspension of [5-bromo-2-[2-(4-methylphenyl)-2-oxoethoxy]benzyl](triphenyl)phosphonium bromide (5.53 g) in ethanol (20 ml) was added at room temperature a 20% solution of sodium ethoxide in ethanol (2.85 g), and the resulting mixture was stirred for 24 hours. After addition of water (15 ml) to the reaction mixture, a solid material was collected by filtration and was washed with water. The solid material were purified by recrystallization (ethanol) to obtain 6-bromo-3-(4-methylphenyl)-2H-1-benzopyran (2.16 g) as colorless crystals.

Workup

  1. filtrationa solid material was collected by filtration
  2. washwas washed with water
  3. customThe solid material were purified by recrystallization (ethanol)

Sources & evidence

ORD record
ord-bed4e0e270044b65b9c1efcc1d4c8796
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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