4-Bromothioanisole → 2-(5-Bromo-2-methylsulfanylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1491138

反応式

HRID 1491138 の反応式
CSc1ccc(Br)cc1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1ccc(C)cc1.FC(F)(F)C1COB(c2ccccc2-c2ccc(-c3ccccn3)nc2)O1.[Ir].[Ir]>CSc1ccc(Br)c(B2OC(C)(C)C(C)(C)O2)c1.CSc1ccc(Br)cc1B1OC(C)(C)C(C)(C)O1

参加物

7

反応物 1

HCID 660374-Bromothioanisole

生成物 2

HCID 1325102612-(5-Bromo-2-methylsulfanylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane収率 74%HCID 178503104HCID 178503104、化合物収率 11%

試薬・触媒・溶媒 4

HCID 2733548Bis(pinacolato)diborane試薬HCID 1349566232-Pyridin-2-yl-5-[2-[4-(trifluoromethyl)-1,3,2-dioxaborolan-2-yl]phenyl]pyridine試薬HCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridium触媒HCID 7809P-Xylene溶媒

反応条件

温度
55 °C

実験手順

Ligand 3f: A mixture of ortho- and meta-borylated products (139 mg, 85% yield, ortho/meta + para = 6.6); ortho-borylated product 4f was obtained by further purification by GPC (101 mg, 62% yield), yellow solid (mp. 88-90 oC)

出典と根拠

ORDレコード
ord-344f37acfe63498da614c14da31d0868
出典データセット
Borylation dataset from Roche

関連ノート

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