Hydrochloric Acid → 4-Acetylphenylboronic acid

HRID 1708055Notes

Reaction equation

HRID 1708055 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]2([CH3:18])OCC[O:14]2)=[CH:9][CH:8]=1.C([O:22][B:23](OC(C)C)[O:24]C(C)C)(C)C.Cl>C1COCC1>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([B:23]([OH:24])[OH:22])=[CH:8][CH:9]=1)(=[O:14])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 6149202-(4-Bromophenyl)-2-methyl-1,3-dioxolaneHCID 178418339Butyllithium

Product 1

HCID 37021224-Acetylphenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (81.6 ml) was added dropwise to a stirred solution of 2-(4-bromophenyl)-2-methyl-1,3-dioxolane (30.0 g) in dry THF (400 ml), under nitrogen, at -75° C. After a period of 1.5 h, triisopropylborate (31.2 ml) was added dropwise at -75° C. The reaction was allowed to warm to room temperature over a 3 h period. Hydrochloric acid (2N; 200 ml) was added and the reaction was allowed to stand at room temperature overnight. The solvent was evaporated and the residue was purified by FCC eluting with ether to give a white solid which was purified by crystallisation from water (200 ml) to give the title compound (14.52 g) as a white crystalline solid m.p. 268°-270° C.

Workup

  1. waitto stand at room temperature overnight
  2. customThe solvent was evaporated
  3. customthe residue was purified by FCC
  4. washeluting with ether
  5. customto give a white solid which
  6. customwas purified by crystallisation from water (200 ml)

Sources & evidence

ORD record
ord-336618d9bd3e414eb0c731648cd6a6cb
Source dataset
uspto-grants-1994_10
Patent number
US05356893

Reaction notes

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