Triisopropyl borate → HCID 58288411, compound

HRID 1476122Notes

Reaction equation

HRID 1476122 reaction equation
C([Li])CCC.[CH2:6]([N:13]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:14]1[CH:19]=[C:18](Br)[CH:17]=[CH:16][C:15]=1[Cl:21])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[B:29](OC(C)C)([O:34]C(C)C)[O:30]C(C)C>CCCCCC.C1COCC1.C(OCC)C>[Cl:21][C:15]1[CH:16]=[CH:17][C:18]([B:29]([OH:34])[OH:30])=[CH:19][C:14]=1[N:13]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 21531Triisopropyl borateHCID 58288335HCID 58288335, compoundHCID 178418339Butyllithium

Product 1

HCID 58288411HCID 58288411, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 21868444Ether tetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Under argon and at −78° C., 20.2 ml (50.42 mmol) of a 2.5 M solution of n-butyllithium in hexane were slowly added dropwise to a solution of 15 g (38.79 mmol) of N,N-dibenzyl-5-bromo-2-chloroaniline in 350 ml of THF/diethyl ether (1:1). The reaction solution was stirred at −78° C. for 60 min, and 14.3 ml (62.1 mmol) of triisopropyl borate were then added slowly. The reaction solution was subsequently stirred at −78° C. for another 15 min, then slowly warmed to room temperature, and stirring at this temperature was continued overnight. 150 ml of ice-water were then metered in. The organic phase was separated off, and the aqueous phase was then extracted three more times with ethyl acetate. The combined organic phases were dried over sodium sulphate. After filtration, the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→4:1). This gave 9 g (66% of theory) of the title compound.

Workup

  1. stirringThe reaction solution was subsequently stirred at −78° C. for another 15 min
  2. temperatureslowly warmed to room temperature
  3. stirringstirring at this temperature
  4. waitwas continued overnight
  5. customThe organic phase was separated off
  6. extractionthe aqueous phase was then extracted three more times with ethyl acetate
  7. dry with materialThe combined organic phases were dried over sodium sulphate
  8. filtrationAfter filtration
  9. customthe solvent was removed under reduced pressure
  10. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→4:1)

Sources & evidence

ORD record
ord-8b71389bbaa548f7a9293e0ba9899b1e
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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