Triisobutyl borate → [3-Bromo-5-(2-methylpropoxy)phenyl]boronic acid

HRID 549564Notes

Reaction equation

HRID 549564 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[C:4](Br)[CH:3]=1.[Li]CCCC.C([O:23][B:24](OCC(C)C)[O:25]CC(C)C)C(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([B:24]([OH:25])[OH:23])[CH:5]=[C:6]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH:7]=1

Participants

5

Reactant 3

HCID 61587Triisobutyl borateHCID 508527731,3-Dibromo-5-isobutoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 53216316[3-Bromo-5-(2-methylpropoxy)phenyl]boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

1,3-Dibromo-5-isobutoxy-benzene (1. g; 3.3 mmol) was dissolved in dry THF (30 ml) in a dry reaction under stirring. The reaction mixture was cooled to −70° C. and n-BuLi (2M; 2.44 ml) was added. The reaction mixture was stirred for 15 min. and triisobutylborate (1.50 ml; 6.5 mmol) was added at −70° C. The temperature was raised to −30° C. and stirred for 1½ hour followed by a temperature increase to room temperature. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate (about 3 ml) and evaporated to dryness. The crude product was purified by prep HPLC (method B). Yield: 430 mg; 49%. HPLC-MS: m/z: 272.9 (M+); Rt: 2.08 min

Workup

  1. stirringThe reaction mixture was stirred for 15 min.
  2. temperatureThe temperature was raised to −30° C.
  3. stirringstirred for 1½ hour
  4. temperatureincrease to room temperature
  5. customThe reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate (about 3 ml)
  6. customevaporated to dryness
  7. customThe crude product was purified by prep HPLC (method B)

Sources & evidence

ORD record
ord-0eabf76e7b4d4309a9f89df460861a6c
Source dataset
uspto-grants-2011_05
Patent number
US07943669B2

Reaction notes

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