Hydrochloric Acid → HCID 19046976, compound

HRID 1780573Notes

Reaction equation

[Mg].Br[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:9]=2)[CH:4]=1.[B:22](OC(C)C)([O:27]C(C)C)[O:23]C(C)C.Cl.[Cl-].[Na+]>O1CCCC1.CCOCC>[CH2:14]([O:13][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH:4]=[C:3]([B:22]([OH:27])[OH:23])[CH:12]=[CH:11]2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: -78 °C

Procedure

The solution of a Grignard compound is prepared from 2.4 g (99.0 mmol) of magnesium and 30 g (89.6 mmol) of 2-bromo-6-octyloxynaphthalene in 250 ml of tetrahydrofuran at 55° C. over a period of 3hours and then added dropwise to a solution of 41.36 ml (179.2 mmol) of triisopropyl borate in 100 ml of tetrahydrofuran cooled to -78° C., and the mixture is stirred overnight. 130 ml of 10% hydrochloric acid are then added dropwise, and the resulting mixture is stirred at room temperature for 1 hour and then distributed between sodium chloride solution and ether, the organic phase is washed with sodium chloride solution, dried over sodium sulfate, concentrated, and the residue recrystallized from hexane, giving 14.5 g of 6-octyloxynaphthalene-2-boronic acid. ##STR65##

Workup

stirringthe resulting mixture is stirred at room temperature for 1 hour
washthe organic phase is washed with sodium chloride solution
dry with materialdried over sodium sulfate
concentrationconcentrated
customthe residue recrystallized from hexane

Sources & evidence

ORD record: ord-aa3110ec930f4ad292191f20f40542f8
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05630962

Reaction notes

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