Hexane → 4-Cyanophenylboronic acid

HRID 1707207Notes

Reaction equation

HRID 1707207 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[B:21](OC)([O:24]C)[O:22]C>O1CCCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([B:21]([OH:24])[OH:22])=[CH:3][CH:4]=1)#[N:7]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8470Trimethyl borateHCID 12162Benzonitrile, 4-bromo-HCID 178418339Butyllithium

Product 1

HCID 27343264-Cyanophenylboronic acidYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

4-Bromobenzonitrile (20 g, 0.1099 m) was dissolved in tetrahydrofuran (240 mls) and hexane (80 mls) and the mixture treated with butyl-lithium (1.6M solution in hexane 80 mls, 0.1204m) at -100° C. The mixture was then stirred for five minutes before adding trimethyl borate (25 mls, 0.2178 m) at -100° C. The mixture was then allowed to warm to 20° C. before adding it to 100 mls of 10% HCL. The organic layer was then separated and the aqueous layer extracted twice with dichloromethane (100 mls). The organic layers were then combined and washed till acid free with water. The solution was then dried using magnesium sulphate and evaporated to give 4-cyanophenyl boronic acid as an off-white solid 93% yield) which was dried under vacuum.

Workup

  1. additionbefore adding it to 100 mls of 10% HCL
  2. customThe organic layer was then separated
  3. extractionthe aqueous layer extracted twice with dichloromethane (100 mls)
  4. washwashed till acid free with water
  5. customThe solution was then dried
  6. customevaporated

Sources & evidence

ORD record
ord-e02e86c6722649c19d1c4d8e45a67838
Source dataset
uspto-grants-1994_10
Patent number
US05352381

Reaction notes

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