1,4-Dibromobenzene → 1093878-29-5

HRID 385719Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.C(O[B:13]1[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]1)(C)C.[Li]C(C)(C)C.[O:27]1[CH2:30][C:29](=[O:31])[CH2:28]1.[NH4+].[Cl-]>C1COCC1.O>[CH3:19][C:16]1([CH3:18])[C:15]([CH3:20])([CH3:21])[O:14][B:13]([C:2]2[CH:7]=[CH:6][C:5]([C:29]3([OH:31])[CH2:30][O:27][CH2:28]3)=[CH:4][CH:3]=2)[O:17]1

Participants

Conditions

Temperature: -78 °C

Procedure

1,4-Dibromobenzene (3.3 g, 13.99 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.91 mL, 14.27 mmol) were taken up in THF (60 mL) and cooled to −78° C. before adding t-BuLi (16.46 mL, 28.0 mmol) dropwise. After stirring at −78° C. for 40 minutes, additional t-BuLi (16.46 mL, 28.0 mmol) was added. After 30 minutes oxetan-3-one (1.01 g, 13.99 mmol) was added and the reaction mixture was allowed to room temperature over 90 minutes. Water was added followed by saturated NH4Cl and the products were extracted into EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by flash silica gel column chromatography (6-50% EtOAc-hexanes) gave the title compound as a white solid.

Workup

waitthe reaction mixture was allowed to room temperature over 90 minutes
extractionthe products were extracted into EtOAc (2×)
washThe combined organic extracts were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the residue by flash silica gel column chromatography (6-50% EtOAc-hexanes)

Sources & evidence

ORD record: ord-58b3f69ce2b04318859e0fe1187b966a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367706B2

Reaction notes

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