Hydrochloric Acid → (4-octylphenyl)boronic Acid

HRID 601447Notes

Reaction equation

C([Li])CCC.[CH2:6]([C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C[O:22][B:23](OC)[O:24]C.Cl>C1COCC1.O>[CH2:6]([C:14]1[CH:19]=[CH:18][C:17]([B:23]([OH:24])[OH:22])=[CH:16][CH:15]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (BuLi, 1.6 M in hexanes, 2.4 mL, 3.8 mmol) was added dropwise to a stirred solution of p-n-octyliodobenzene (1.0 g, 3.2 mmol) in dry THF (15 mL) at −78° C. under nitrogen. After stirring for 30 minutes and maintaining the temperature at −78° C., trimethylborate (0.4 g, 3.8 mmol) was added dropwise. The system was allowed to return to room temperature after 1 hour and was left stirring under nitrogen overnight. Concentrated HCl (8 mL) and water (15 mL) were then added and stirring was continued for 2 hours. The mixture was extracted with ether (15 3 mL). The ethereal phase was combined and was washed with brine and water (20 2 mL), dried with MgSO4, and the solvent removed in vacuo to give p-n-octylphenylboronic acid as a white solid (0.63 g, 84% yield).

Workup

waitto return to room temperature after 1 hour
waitwas left
stirringstirring under nitrogen overnight
stirringstirring
waitwas continued for 2 hours
extractionThe mixture was extracted with ether (15 3 mL)
washwas washed with brine and water (20 2 mL)
dry with materialdried with MgSO4
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-d34cc3a3c6e549849778467f5e0bfa86
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902363B2

Reaction notes

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