Hydrochloric Acid → 4-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)

HRID 1459095Notes

Reaction equation

HRID 1459095 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:8]=1.[B:22](OC)([O:25]C)[O:23]C.Cl>C1COCC1>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([B:22]([OH:25])[OH:23])=[CH:8][CH:9]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 145298p-Bromophenyl octyl etherHCID 178418339Butyllithium

Product 1

HCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (23 ml, 2.5M in hexane, 0.058 mol) was added dropwise to a stirred, cooled (-78° C.) solution of compound 26 (15.00 g, 0.053 mol) in dry THF (168 ml) under dry nitrogen. The reaction mixture was maintained under these conditions for 2.5 h and then a solution of trimethyl borate (10.98 g, 0.106 mol) in dry THF (50 ml) was added dropwise at -78° C. The reaction mixture was allowed to warm to room temperature overnight and then stirred for 1 h with 10% hydrochloric acid (120 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 yield an off white solid.

Workup

  1. temperatureThe reaction 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 yield an off white solid

Sources & evidence

ORD record
ord-13e9cbad7b884e99a537c3abdccb5e9a
Source dataset
uspto-grants-1998_12
Patent number
US05853613

Reaction notes

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