1,3-Dibromobenzene → 2-(3,5-Dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1490553Notes

Reaction equation

HRID 1490553 reaction equation
Brc1cccc(Br)c1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC1CCCC1.C[OH2+].C[OH2+].[Ir].[Ir].c1ccc(N2B(B3Nc4ccccc4N3c3ccccn3)Nc3ccccc32)nc1>CC1(C)OB(c2cc(Br)cc(Br)c2)OC1(C)C

Participants

6

Reactant 1

HCID 79271,3-Dibromobenzene

Product 1

HCID 534290472-(3,5-Dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 98%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaboroleReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 138539Cyclopentyl methyl etherSolvent

Conditions

Temperature
100 °C

Procedure

The general procedure A was followed using 1,3-dibromobenzene (59.0 uL, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 100 oC. 5i was obtained as white solid (178.2 mg, 98%) after purification by silica gel flash chromatography (EtOAc/PE=1:50 v/v). m.p.: 60-62 oC.

Sources & evidence

ORD record
ord-2db5109eed8f40abb3af99be6905eebf
Source dataset
Borylation dataset from Roche

Reaction notes

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