2'-Bromoacetanilide → HCID 178474077, compound

HRID 1490818Notes

Reaction equation

HRID 1490818 reaction equation
CC(=O)Nc1ccccc1Br>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CCCC[N+](CCCC)(CCCC)CCCC.C[OH2+].C[OH2+].Cc1ccc(-c2ccc(CS(=O)(=O)[O-])cn2)nc1.[Ir].[Ir]>CC(=O)Nc1cc(B2OC(C)(C)C(C)(C)O2)ccc1Br.CC(=O)Nc1ccc(B2OC(C)(C)C(C)(C)O2)cc1Br

Participants

7

Reactant 1

HCID 1364162'-Bromoacetanilide

Product 2

HCID 178474016HCID 178474016, compoundYield 27%HCID 178474077HCID 178474077, compoundYield 38%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 165587889Tetrabutylazanium {5'-methyl-[2,2'-bipyridin]-5-yl}methanesulfonateReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Following general procedure F using 2‐bromoacetanilide (53.5 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1a (3.8 mg, 0.0075 mmol) in THF (1.25 mL). The reaction was stirred at 70 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internalstandard 1,2‐dimethoxyethane showed 1:1.4 meta:para borylation in 65% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1‐6:4) to give the title compound (as a 1:1.7:1.3 mixture of meta:para:SM ratio, as determined by 1 H NMR) as a colourless oil. NMR yields have been used for all comparisons.

Sources & evidence

ORD record
ord-747d177d807e42c3b290322525437143
Source dataset
Borylation dataset from Roche

Reaction notes

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