Trimethyl borate → methyl di(p-chlorophenyl)borinate

HRID 751321Notes

Reaction equation

HRID 751321 reaction equation
[CH3:1][O:2][B:3](OC)OC.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([Mg]Br)=[CH:11][CH:10]=1>O1CCCC1>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([B:3]([C:12]2[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=2)[O:2][CH3:1])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 8470Trimethyl borateHCID 178478191HCID 178478191, compound

Product 1

HCID 11482468methyl di(p-chlorophenyl)borinateYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trimethylborate (2.2 ml, 1.92×10−2 mol) is added dropwise to a freshly prepared solution of p-chlorophenyl magnesium bromide (40.4 ml, 1 M, 4.04×10−2 mol) in tetrahydrofuran (60 ml) under argon at −78° C. The mixture is warmed to room temperature and stirred overnight. The solution is cooled to −78° C. and excess grignard reagent is destroyed by the dropwise addition of methanol until no more effervescence is observed. The solvents are removed in vacuo and the residue dissolved in diethyl ether and washed with water. The organic layer is dried (MgSO4), filtered and the solvents removed in vacuo to give methyl di(p-chlorophenyl)borinate (4.60 g, 92%) as a solid which was used without further purification.

Workup

  1. temperatureThe solution is cooled to −78° C.
  2. customexcess grignard reagent is destroyed by the dropwise addition of methanol until no more effervescence
  3. customThe solvents are removed in vacuo
  4. dissolutionthe residue dissolved in diethyl ether
  5. washwashed with water
  6. dry with materialThe organic layer is dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-fdfe0a805e1345779e827afcbd38efb4
Source dataset
uspto-grants-2008_07
Patent number
US07405304B2

Reaction notes

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