Hydrochloric Acid → 2-Octylindane-5-boronic acid

HRID 1770166Notes

Reaction equation

HRID 1770166 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:5]2.C([Li])CCC.C([O:27][B:28](OC(C)C)[O:29]C(C)C)(C)C.Cl>CCCCCC.C1COCC1>[CH2:11]([CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([B:28]([OH:29])[OH:27])[CH:3]=2)[CH2:7]1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 235091535-Bromo-2-octylindanHCID 178418339Butyllithium

Product 1

HCID 220990862-Octylindane-5-boronic acidYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

In a 200 ml-reaction vessel, 3.16 g (1.02×10-2M) of 5-bromo-2-n-octylindan and 45 ml of dry THF were placed. To the mixture, 1.5M-solution of n-butyllithium in 7.2 ml of hexane was added dropwise in 20 minutes at -70° C. under argon atmosphere, followed by stirring for 2 hours at -70° C. To the above mixture, a solution of 4.14 g (2.20×10-2M) of triisopropylborate in 9 ml of dry THF was added dropwise in 20 minutes below -70° C., followed by stirring for 1 hour at the same temperature, gradual restoration to room temperature and further stirring for 20 hours. After the reaction, 15 ml of 10%-HCl aqueous solution was added dropwise to the reaction mixture to be decomposed under cooling, followed by extraction with ether. The ether layer was washed with water and dried with anhydrous sodium sulfate, followed by distilling-off of the solvent and purification by silica gel column chromatography to obtain 1.96 g of 2-octylindan-5-boronic acid (Yield: 70%).

Workup

  1. stirringby stirring for 1 hour at the same temperature, gradual restoration to room temperature
  2. stirringfurther stirring for 20 hours
  3. additionwas added dropwise to the reaction mixture
  4. temperatureunder cooling
  5. extractionfollowed by extraction with ether
  6. washThe ether layer was washed with water
  7. dry with materialdried with anhydrous sodium sulfate
  8. distillationfollowed by distilling-off of the solvent and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-b34275ec2696456b881065695c6434f0
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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