Trimethyl borate → HCID 54595780, compound

HRID 1360844Notes

Reaction equation

HRID 1360844 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[B:21](OC)([O:24]C)[O:22]C.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[O:14]([CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[B:21]([OH:24])[OH:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 8470Trimethyl borateHCID 25517Ammonium ChlorideHCID 131696961-Bromo-2-(phenoxymethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 54595780HCID 54595780, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

90 ml of n-butyllithium (1.6 M) in solution in hexane are added dropwise at −70° C. to 36 g of 1-bromo-2-(phenoxymethyl)benzene, obtained in step 1.1, in solution in 150 ml of tetrahydrofuran. After 2 hours at −70° C., 16 ml of trimethyl borate are introduced dropwise. The temperature of the reaction medium is allowed to rise to −30° C. The medium is hydrolyzed with a saturated ammonium chloride solution, and then extracted with ethyl acetate and the organic phase is dried with anhydrous sodium sulfate. After evaporation, 33 g of a white solid are obtained.

Workup

  1. customto rise to −30° C
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase is dried with anhydrous sodium sulfate
  4. customAfter evaporation, 33 g of a white solid
  5. customare obtained

Sources & evidence

ORD record
ord-a8f47c8392e94d3f81855d558347bcfa
Source dataset
uspto-grants-2011_02
Patent number
US07879889B2

Reaction notes

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