Bromine → HCID 15338831, compound

HRID 1789392Notes

Reaction equation

HRID 1789392 reaction equation
BrBr.C[C@@H]1C2C(=CC=CC=2)C[C@@H]1C(=O)C.[Br:16][C:17]1([C:27](=[O:29])[CH3:28])[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]1[CH3:26].[Br:30]CC([C@H]1CC2C(=CC=CC=2)[C@H]1C)=O>C(Cl)Cl>[Br:30][CH2:28][C:27]([C:17]1([Br:16])[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]1[CH3:26])=[O:29]

Participants

6

Reactant 4

HCID 24408Bromine2×HCID 18609506HCID 18609506, compoundHCID 20188225HCID 20188225, compoundHCID 54146119HCID 54146119, compound

Product 1

HCID 15338831HCID 15338831, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Bromine in methylene chloride is slowly added to a stirred solution of cis-1-(2,3-dihydro-1-methyl-1H-inden-2-yl)ethanone (34.8 g) in methylene chloride (835 ml), while keeping the temperature at +10° C. The reaction is followed by GLC. The first products are the isomers of 1-(2-bromo-2,3-dihydro-1-methyl-1H-inden-2-yl)ethanone and cis-2-bromo-1-(2,3-dihydro-1-methyl-1H-inden-2-yl)ethanone. When the added amount of bromine is about 0.3 mol, only the final product, 2-bromo-1-(2-bromo-2,3-dihydrol-methyl-1H-inden-2-yl)ethanone is visible in the chromatogram and the mono bromo products cannot be seen in the chromatogram any more. The methylene chloride solution is washed with water, then several times with the diluted NaHCO3 solution and finally with water. The solvent is dried with Na2SO4 and evaporated to dryness.

Workup

  1. customat +10° C

Sources & evidence

ORD record
ord-8626b45b275c4e28bae2be02833668e2
Source dataset
uspto-grants-1987_08
Patent number
US04689339

Reaction notes

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