Trimethyl borate → HCID 23437316, compound

HRID 2120026Notes

Reaction equation

HRID 2120026 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C([Li])CCC.C[O:29][B:30](OC)[O:31]C>O1CCCC1>[F:1][C:2]1[C:3]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:4]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:5]([F:8])=[CH:6][C:7]=1[B:30]([OH:31])[OH:29]

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 23437314HCID 23437314, compoundHCID 178418339Butyllithium

Product 1

HCID 23437316HCID 23437316, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1,4-Difluoro-2,3-dihexyloxybenzene (11.2 g, 0.036 mol) was stirred, under nitrogen, in anhydrous tetrahydrofuran (150 ml). The reaction mixture was cooled to −78° C. and then butyl lithium (1.6M in hexanes, 24.38 ml, 0.039 mol) was added via cannular over one hour. Stirring was continued at −78° C. for 2 hours. This temperature was maintained whilst a solution of trimethylborate (4.05 g, 0.039 mol) in dry tetrahydrofuran (100 ml) was added drop-wise. The cooling bath was then removed and the reaction was stirred overnight at room temperature. Addition of HCl (1M, 36 ml) dissolved the white suspension and a yellow solution was formed. Extraction was performed with toluene (2×100 ml), the combined organics extracts were then washed with water (2×50 ml), dried with magnesium sulphate. Removal of the drying agent by filtration and the solvent in vacuo yielded a brown oil containing the crude product (11.95 g, 93%). The product was used in the next step without further purification.

Workup

  1. additionwas added drop-wise
  2. customThe cooling bath was then removed
  3. stirringthe reaction was stirred overnight at room temperature
  4. additionAddition of HCl (1M, 36 ml)
  5. dissolutiondissolved the white suspension
  6. customa yellow solution was formed
  7. extractionExtraction
  8. washthe combined organics extracts were then washed with water (2×50 ml)
  9. dry with materialdried with magnesium sulphate
  10. customRemoval of the drying agent
  11. filtrationby filtration
  12. customthe solvent in vacuo yielded a brown oil
  13. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-dd22cb94814443ffb815b13332e4d8e7
Source dataset
uspto-grants-2004_02
Patent number
US06689290B2

Reaction notes

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