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Benzene, 1-bromo-3-(trifluoromethyl)- → 2-[3-Bromo-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1490552
Notes
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Reaction equation

HRID 1490552 reaction equation
FC(F)(F)c1cccc(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(C(F)(F)F)c2)OC1(C)C
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

6

Reactant 1

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-

Product 1

HCID 113141192-[3-Bromo-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 99%

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 76001521

Conditions

Temperature
100 °C

Procedure

The general procedure A was followed using 1-bromo-3-(trifluoromethyl)benzene (67.5 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. 5h was obtained as colorless oil (173.1 mg, 99%) after purification by silica gel flash chromatography (EtOAc/PE=1:30 v/v).

Sources & evidence

ORD record
ord-4651aa72b42b47c9a0457945292dda09
Source dataset
Borylation dataset from Roche
DOI
10.1021/jacs.5b05252

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
Bis(1,5-cyclooctadiene)dimethoxydiiridium
Catalyst
HCID 138539Cyclopentyl methyl etherSolvent