2-Bromophenol → 8-Bromo-2H-1-benzopyran-3(4H)-one

HRID 2188794Notes

Reaction equation

HRID 2188794 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Mg+2].[Cl-].[Cl-].[C:12](#N)[CH:13]=[CH2:14].[OH-:16].[Na+]>C1COCC1.CCN(CC)CC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[O:8][CH2:14][C:13](=[O:16])[CH2:12]2

Participants

7

Reactant 4

HCID 72442-Bromophenol2×HCID 7855AcrylonitrileHCID 14798Sodium HydroxideHCID 5360315Magnesium Chloride

Product 1

HCID 190871488-Bromo-2H-1-benzopyran-3(4H)-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

8-Bromochroman-3-one 28B was prepared from 2-bromophenol in a manner similar to that described in the literature (J. Med. Chem., 1988, 689): Reaction of 2-bromophenol with paraformadehyde (MgCl2, NEt3, THF, 75° C., 4 h), followed by treatment with acrylonitrile (neat, Dabco, 95° C., 18 h), and hydrolysis with 10% NaOH (100° C., 4 h) afforded 28A. Compound 28A was reacted with DPPA (NEt3, toluene, 110° C., 2 h) followed by treatment with 6N HCl (85° C., 2 h) to afford 8-bromochroman-3-one 28B.

Sources & evidence

ORD record
ord-19eaa2b4d97a44439895e337ed1a1741
Source dataset
uspto-grants-2012_12
Patent number
US08324213B2

Reaction notes

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