Bromine → 4,5-dimethyl-6-oxo-7,8-dihydro-7-bromo-7-isopropyl-6H-indeno[5,4-b]furan-2-carboxylic acid

HRID 1579627Notes

Reaction equation

HRID 1579627 reaction equation
[CH3:1][C:2]1[C:10]2[O:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=2[C:8]2[CH2:7][CH:6]([CH:17]([CH3:19])[CH3:18])[C:5](=[O:20])[C:4]=2[C:3]=1[CH3:21].[Br:22]Br.S(=O)(O)[O-].[Na+]>C(O)(=O)C.Br>[CH3:1][C:2]1[C:10]2[O:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=2[C:8]2[CH2:7][C:6]([Br:22])([CH:17]([CH3:18])[CH3:19])[C:5](=[O:20])[C:4]=2[C:3]=1[CH3:21]

Participants

6

Reactant 3

HCID 24408BromineHCID 215689444,5-Dimethyl-6-oxo-7-isopropyl-7,8-dihydro-6H-indeno[5,4-b]furan-2-carboxylic acidHCID 23665763Sodium Bisulfite

Product 1

HCID 215689584,5-dimethyl-6-oxo-7,8-dihydro-7-bromo-7-isopropyl-6H-indeno[5,4-b]furan-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 176Acetic AcidSolvent2×

Procedure

A solution of 4,5-dimethyl-6-oxo-7,8-dihydro-7-isopropyl-6H-indeno[5,4-b]furan-2-carboxylic acid (0.01 mole) in acetic acid (60 ml.) is treated with 48% hydrobromic acid (1 drop) then with bromine (0.01 mole) in acetic acid (10 ml.) during a ten minute period. The solution is poured into ice water (300 ml.) containing sodium bisulfite (1 g.) to afford 4,5-dimethyl-6-oxo-7,8-dihydro-7-bromo-7-isopropyl-6-H-indeno[5,4-b]furan-2-carboxylic acid.

Sources & evidence

ORD record
ord-b35d7ec60ebc48a1a56d5a6be522bb76
Source dataset
uspto-grants-1976_01
Patent number
US03931239

Reaction notes

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