Hydrochloric Acid → 2,4-Dibromo-beta-butylbenzeneethanol

HRID 745276Notes

Reaction equation

HRID 745276 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:14][CH2:15][CH2:16][CH3:17])[C:10](OC)=[O:11].O.O.[I-].[Li+].[BH4-].[Na+].Cl>C(#N)C>[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][OH:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 12343320Methyl 2,4-dibromo-alpha-butylbenzeneacetateHCID 23688289Lithium iodide (LiI), dihydrate

Product 1

HCID 123433642,4-Dibromo-beta-butylbenzeneethanolYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 16.5 parts of methyl 2,4-dibromo-α-butylbenzeneacetate, 11.5 parts of lithium iodide dihydrate and 180 parts of acetonitrile is stirred till all solid enters solution. Then there are added portionwise 3.6 parts of sodium borohydride. Upon completion, the whole is heated to reflux and stirring is continued overnight at reflux temperature. After cooling, the reaction mixture is acidified with a diluted hydrochloric acid solution and poured onto water. The product is extracted with 2,2'-oxybispropane. The extract is washed with water, dried, filtered and evaporated, yielding 15 parts (100%) of 2,4-dibromo-β-butylbenzeneethanol as a residue.

Workup

  1. temperatureUpon completion, the whole is heated
  2. temperatureto reflux
  3. stirringstirring
  4. temperatureat reflux temperature
  5. temperatureAfter cooling
  6. additionpoured onto water
  7. extractionThe product is extracted with 2,2'-oxybispropane
  8. washThe extract is washed with water
  9. customdried
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-99f51b1d1de5474dab62edc6037e9488
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

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