2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 131736572, compound

HRID 1479122Notes

Reaction equation

HRID 1479122 reaction equation
[CH3:1][C:2]1([CH3:28])[C:14]2[CH:13]=[C:12]([C:15]3[C:20]4[S:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=5[C:19]=4[CH:18]=[CH:17][CH:16]=3)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C([Li])(CC)C.C(O[B:38]1[O:42][C:41]([CH3:44])([CH3:43])[C:40]([CH3:46])([CH3:45])[O:39]1)(C)C>C1COCC1.C1CCCCC1>[CH3:1][C:2]1([CH3:28])[C:14]2[CH:13]=[C:12]([C:15]3[C:20]4[S:21][C:22]5[C:27]([B:38]6[O:42][C:41]([CH3:44])([CH3:43])[C:40]([CH3:46])([CH3:45])[O:39]6)=[CH:26][CH:25]=[CH:24][C:23]=5[C:19]=4[CH:18]=[CH:17][CH:16]=3)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

6

Reactant 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 117601456HCID 117601456, compoundHCID 178418400CID 53628100

Product 1

HCID 131736572HCID 131736572, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Into a solution of 4-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]thiophene (10.637 g, 28.3 mmol) in THF (200 ml), a solution of sec-butyllithium 1.4 M (27.2 ml, 38.1 mmol) in cyclohexane at −78° C. was added slowly. The resulting mixture was stirred at −78° C. for 2 hours before quenching with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (8.65 ml, 42.4 mmol) added at one portion. The mixture was gradually warmed to room temperature, stirred overnight, and then quenched with methanol. The solvent was evaporated. The residue was purified by column chromatography on silica gel with a heptane/DCM (4/1 to 1/1) eluent and then precipitation in MeOH to yield 2-(6-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.3 g, 65.5% yield) as a white solid.

Workup

  1. additionadded at one portion
  2. temperatureThe mixture was gradually warmed to room temperature
  3. stirringstirred overnight
  4. customquenched with methanol
  5. customThe solvent was evaporated
  6. customThe residue was purified by column chromatography on silica gel with a heptane/DCM (4/1 to 1/1) eluent
  7. customprecipitation in MeOH

Sources & evidence

ORD record
ord-8b642c933dd248e1879a232627af4c64
Source dataset
uspto-grants-2016_08
Patent number
US09406892B2

Reaction notes

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