Hydrochloric Acid → 5-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1684914Notes

Reaction equation

HRID 1684914 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1(=[O:15])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[Br:16]Br.Cl>O.C(OCC)C>[Br:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH2:8][CH2:7][CH2:6][C:5]2=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 107241-TetraloneHCID 24408BromineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 108895725-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

2.21 g of AlCl3 are placed in a round-bottomed flask, to which 0.91 ml of 3,4-dihydro-2H-naphth-1-one is added over 10 min and 0.41 ml of Br2 is added over 5 min, and the mixture is heated at 80° C. for 10 min. It is allowed to return to ambient temperature and a solution comprising 20 g of ice and 2.7 ml of concentrated hydrochloric acid is added thereto. The mixture is then diluted with water and diethyl ether. The organic phase is subsequently separated, dried and concentrated under reduced pressure. The residue is purified by reverse phase preparative chromatography. 172 mg of compound are obtained.

Workup

  1. additionis added over 10 min
  2. customto return to ambient temperature
  3. additionis added
  4. customThe organic phase is subsequently separated
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by reverse phase preparative chromatography

Sources & evidence

ORD record
ord-1f2e549f1b2f43aabd803a714d03a669
Source dataset
uspto-grants-2012_04
Patent number
US08148370B2

Reaction notes

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