Bromine → 8-Bromo-6-acetyltetralin

HRID 1352723Notes

Reaction equation

HRID 1352723 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH2:14][CH2:13][CH2:12][CH2:11]2)(=[O:7])[CH3:6].[Br:18]Br>>[Br:18][C:16]1[CH:17]=[C:8]([C:5](=[O:7])[CH3:6])[CH:9]=[C:10]2[C:15]=1[CH2:14][CH2:13][CH2:12][CH2:11]2

Participants

4

Reactant 3

HCID 24408BromineHCID 698856-AcetyltetralinHCID 6451240Aluminum(III) Chloride

Product 1

HCID 187708638-Bromo-6-acetyltetralin

Procedure

To AlCl3 (9.9 g, 75 mmol) is added dropwise 6-acetyltetralin (5.25 g, 30 mmol) under mechanical stirring at RT. After 20 minutes at 70° C. the reaction is cooled to RT and treated in small portions with Br2 (5.76 g [=1.86 ml], 36 mmol) over a period of 30 minutes. After that the mixture is stirred for further 60 minutes at 85° C. After cooling down to RT and addition of ice-water (450 ml) the compound is extracted with methylene chloride and purified on silica gel using a mixture of cyclo-hexane/ethyl acetate 2/1 to 1/1 obtaining the product as a pale yellow solid.

Workup

  1. temperatureAfter 20 minutes at 70° C. the reaction is cooled to RT
  2. stirringAfter that the mixture is stirred for further 60 minutes at 85° C
  3. temperatureAfter cooling down to RT
  4. extractionis extracted with methylene chloride
  5. custompurified on silica gel using
  6. additiona mixture of cyclo-hexane/ethyl acetate 2/1 to 1/1 obtaining the product as a pale yellow solid

Sources & evidence

ORD record
ord-6804b3be1f724259902057e5f01f28a5
Source dataset
uspto-grants-2007_05
Patent number
US07220774B2

Reaction notes

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