Hydrochloric Acid → HCID 21834830, compound

HRID 400264Notes

Reaction equation

HRID 400264 reaction equation
C([Li])CCC.[Br:6][C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](Br)=[CH:9][C:8]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C[O:27][B:28](OC)[O:29]C.Cl>CCCCCC.C(OCC)C>[Br:6][C:7]1[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:9][C:10]([B:28]([OH:29])[OH:27])=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 21834840HCID 21834840, compoundHCID 178418339Butyllithium

Product 1

HCID 21834830HCID 21834830, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

4-Bromo-2,5-diphenylbenzeneboronic acid is prepared as follows: A solution of n-butyllithium (1.6 M, 15 ml) in hexane is added slowly to a cooled (-40° C.) solution of 1,4-di-bromo-2,5-diphenylbenzene (25 mmol) in diethylether (100 ml). This mixture is allowed to warm to room temperature and is stirred for 2 hours. This solution is transferred into a dropping funnel and added to a cooled (-60° C.) solution of trimethylborate (74 mmol) in ether (200 ml). It is then stirred for 8 hours at room temperature. After hydrolysis with aqueous HCl (2M, 150 ml), the layers are separated and the aqueous layer is extracted with ether (100 ml). The solvent is then removed from the combined organic layers and water (5 ml) and petroleum ether (100) are added. The precipitate is recovered by filtration, and recrystallized from toluene.

Workup

  1. customThis solution is transferred into a dropping funnel
  2. additionadded to
  3. stirringIt is then stirred for 8 hours at room temperature
  4. customthe layers are separated
  5. extractionthe aqueous layer is extracted with ether (100 ml)
  6. customThe solvent is then removed from the combined organic layers and water (5 ml) and petroleum ether (100)
  7. additionare added
  8. filtrationThe precipitate is recovered by filtration
  9. customrecrystallized from toluene

Sources & evidence

ORD record
ord-5dbdc164c1d24b6bb93562454bff936a
Source dataset
uspto-grants-1998_10
Patent number
US05827927

Reaction notes

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