Hydrochloric Acid → HCID 66782681, compound

HRID 1096571Notes

Reaction equation

HRID 1096571 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:3]=1Br.CCCCCC.C([Li])CCC.[B:32](OC(C)C)([O:37]C(C)C)[O:33]C(C)C.Cl>C1COCC1>[C:14]1([C:5]2[CH:4]=[C:3]([B:32]([OH:37])[OH:33])[C:2]([Br:1])=[CH:7][C:6]=2[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 24865705HCID 24865705, compoundHCID 178418339Butyllithium

Product 1

HCID 66782681HCID 66782681, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-100 °C

Procedure

To a 100 ml Schlenk reaction vessel were added under a nitrogen atmosphere 755 mg (1.95=mol) of 1,2-dibromo-4,5-diphenylbenzene synthesized in 2) and 12 ml of THF. The solution was cooled to −100° C. and 1.3 ml (2.1 mmol) of a hexane solution of n-butyllithium (manufactured by Kanto Chemical Co., Ltd., 1.59M) was added dropwise. After 30 minutes of aging, 472 my (2.51 mmol) of triisopropyl borate (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise. After the temperature was gradually raised to room temperature, 3N hydrochloric acid was added and phase separation was conducted. The organic phase was concentrated under reduced pressure to obtain 770 my of a white solid (2-phenyl-5-bromo-4-biphenylboronic acid).

Workup

  1. temperatureAfter the temperature was gradually raised to room temperature
  2. customphase separation
  3. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3208202022444fc0bc5532e8883299f6
Source dataset
uspto-grants-2012_03
Patent number
US08138355B2

Reaction notes

Loading…