Water → 4,4,5,5-Tetramethyl-2-(2-methylphenyl)-1,3,2-dioxaborolane

HRID 634066Notes

Reaction equation

HRID 634066 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Mg]Br.C(O[B:14]1[O:18][C:17]([CH3:20])([CH3:19])[C:16]([CH3:22])([CH3:21])[O:15]1)(C)C.O>C1COCC1>[CH3:21][C:16]1([CH3:22])[C:17]([CH3:20])([CH3:19])[O:18][B:14]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[O:15]1

Participants

5

Reactant 3

HCID 962Water2×HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178424303HCID 178424303, compound

Product 1

HCID 107040084,4,5,5-Tetramethyl-2-(2-methylphenyl)-1,3,2-dioxaborolane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 200 ml (0.21 mol) of 1.07 M solution of 2-methyl phenylmagnesiumbromide in THF, 49.3 g (0.27 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added at room temperature. The resulting solution was stirred for 15 min at the same temperature, and then 50 ml of water was added. The formed mixture was poured into 500 ml of water, and crude product was extracted with 3×200 ml of ethyl acetate. The combined organic extract was dried over Na2SO4 and then evaporated to dryness. Fractional distillation of the residue in vacuum gave colorless oil, b.p. 81-84° C./3 mmm Hg. Yield 33.1 g (57%). Anal. calc. for C13H19BO2: C, 71.59; H, 8.78. Found: C, 71.78; H, 8.65. 1H NMR (CDCl3): 7.78 (m, 1H, 6-H), 7.33 (m, 1H, 5-H), 7.16-7.19 (m, 2H, 3, 4-H), 2.56 (s, 3H, Me in 2-MeC6H4), 1.36 (s, 12H, Bpin).

Workup

  1. extractionwas extracted with 3×200 ml of ethyl acetate
  2. extractionThe combined organic extract
  3. dry with materialwas dried over Na2SO4
  4. customevaporated to dryness
  5. distillationFractional distillation of the residue in vacuum
  6. customgave colorless oil, b.p. 81-84° C./3 mmm Hg

Sources & evidence

ORD record
ord-bc1e5e987287438090ac631a9d45bf2b
Source dataset
uspto-grants-2016_04
Patent number
US09321858B2

Reaction notes

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