Hydrochloric Acid → HCID 19380609, compound

HRID 466495Notes

Reaction equation

HRID 466495 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:8]=[C:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:10]=[C:11]([F:13])[CH:12]=1.[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C.Cl>C1COCC1>[F:6][C:7]1[CH:8]=[C:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:10]=[C:11]([F:13])[C:12]=1[B:19]([OH:24])[OH:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 157519781,3-Difluoro-5-pentylbenzeneHCID 178418339Butyllithium

Product 1

HCID 19380609HCID 19380609, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of n-butyllithium (10.4M in hexane; 2.70 ml, 0.028 mol) was added dropwise to a stirred, cooled (-78° C.) solution of compound 13 (5.00 g, 0.027 mol) in dry THF (60 ml) under dry nitrogen. The stirred mixture was maintained under these conditions for 2.5 h and a previously cooled solution of tri-isopropyl borate (10.22 g, 0.054 mol) in dry THF (50 ml) was added dropwise at -78° C. The stirred mixture was allowed to warm to room temperature overnight and stirred for 1 h with 10% hydrochloric acid (30 ml). The product was extracted into ether (twice), and the combined ethereal extracts were washed with water and dried (MgSO4). The solvent was removed in vacuo to give a colourless solid.

Workup

  1. temperatureThe stirred mixture was maintained under these conditions for 2.5 h
  2. extractionThe product was extracted into ether (twice), and the combined ethereal extracts
  3. washwere washed with water
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customto give a colourless solid

Sources & evidence

ORD record
ord-6154afb57e054b5183ec35d6077b2941
Source dataset
uspto-grants-1992_10
Patent number
US05156763

Reaction notes

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