Tetrahydrofuran → Boronic Acid

HRID 1751325Notes

Reaction equation

HRID 1751325 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([N:7]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.O1CCCC1.[Li]CCCC.CCCCCC.[B:37](OC(C)C)([O:42]C(C)C)[O:38]C(C)C>O>[BH:37]([OH:42])[OH:38].[C:14]1([N:7]([C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[BH:37]([OH:42])[OH:38]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 21531Triisopropyl borateHCID 6428384-BromotriphenylamineHCID 178418244HCID 178418244, compound

Product 2

HCID 61668Boronic AcidYield 460.1%HCID 178514835HCID 178514835, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Also, triphenylamine boronic acid product was synthesized as follows. Under an argon (Ar) atmosphere, 246 g of 4-bromotriphenylamine (commercially available product), and 1500 ml of anhydrous tetrahydrofuran were placed in a 5 liter flask, and 570 ml of 1.6M n-BuLi/hexane solution was added dropwise over 3 hours at −60° C. After 30 minutes, 429 g of triisopropyl borate was added dropwise over 1 hour. Then, reaction overnight at ambient temperature was allowed. After the reaction, 2 liters of water was added dropwise, and after that, the mixture was extracted and the liquid was separated using 2 liters of toluene. The organic layer was concentrated, recrystallized, filtered, dried and 160 g of white boronic acid product, a target compound, was obtained.

Workup

  1. customThen, reaction overnight at ambient temperature
  2. additionwas added dropwise
  3. extractionafter that, the mixture was extracted
  4. customthe liquid was separated
  5. concentrationThe organic layer was concentrated
  6. customrecrystallized
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-a012cd0d25594700943fbbf2ddd392dd
Source dataset
uspto-grants-2015_10
Patent number
US09159932B2

Reaction notes

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