2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-(6-Chlorobenzofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1403376Notes

Reaction equation

HRID 1403376 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][O:8][C:4]=2[CH:3]=1.[Li]CCCC.[CH3:16][C:17]1([CH3:28])[C:21]([CH3:23])([CH3:22])[O:20][B:19](OC(C)C)[O:18]1>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[C:7]([B:19]3[O:20][C:21]([CH3:23])([CH3:22])[C:17]([CH3:28])([CH3:16])[O:18]3)[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178424386-Chloro-1-benzofuranHCID 178418339Butyllithium

Product 1

HCID 706648872-(6-Chlorobenzofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-1-benzofuran (2 g, 13.11 mmol) in tetrahydrofuran (30 mL) was added n-BuLi (10 mL, 2.5N) at −78° C. and stirred for 1.5 h. Then 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane (4.4 g, 23.65 mmol) was added and stirred for 1.5 h. The reaction solution was quenched by water (100 mL), extracted with ethyl acetate (3×50 mL), dried over anhydrous magnesium sulfate and concentrated under vacuum to give 2-(6-chloro-1-benzofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a reddish crude solid (3 g, crude).

Workup

  1. stirringstirred for 1.5 h
  2. customThe reaction solution was quenched by water (100 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-803e0da02447406d8dce976e3477f492
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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