Hydrochloric Acid → HCID 66782681, compound

HRID 1015956Notes

Reaction equation

HRID 1015956 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, compoundYield 111.9%

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 mmol) of 1,2-dibromo-4,5-diphenylbenzene synthesized in Synthetic Example 4 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 mg (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 mg of a white solid.

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-4ae007762185431e8b22887005a24049
Source dataset
uspto-grants-2011_07
Patent number
US07985885B2

Reaction notes

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