Neopentyl glycol → 4'-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-[1,1'-biphenyl]-2-ol

HRID 338464Notes

Reaction equation

HRID 338464 reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].CC1(C)C(C)(C)O[B:11]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]([OH:28])=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)O1>O1CCOCC1>[CH3:1][C:2]1([CH3:7])[CH2:5][O:6][B:11]([C:16]2[CH:17]=[CH:18][C:19]([C:22]3[C:23]([OH:28])=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:20][CH:21]=2)[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 31344Neopentyl glycolHCID 592678134'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-ol

Product 1

HCID 866987994'-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-[1,1'-biphenyl]-2-olYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,2-dimethylpropane-1,3-diol (4.0 g, 38 mmol) and 4′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-ol (1.0 g, 3.4 mmol) in 1,4-dioxane (2 mL) was subjected to microwave irradiation at 210° C. for 1 hour. The cooled reaction mixture was partitioned between water (50 mL) and 1:1 EtOAc/heptane (25 mL:25 mL). The organic layer was washed with water (30 mL) and brine (30 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound (0.95 g, 99% yield). GC/MS, M=282 at 5.31 min. 1H NMR (500 MHz, CDCl3) δ 7.94 (d, J=7.81 Hz, 2H), 7.48 (d, J=7.81 Hz, 2H), 7.31-7.26 (m, 2H), 7.03-6.98 (m, 2H), 3.82 (s, 4H), 1.08-1.04 (m, 6H).

Workup

  1. customirradiation at 210° C. for 1 hour
  2. customThe cooled reaction mixture
  3. customwas partitioned between water (50 mL) and 1:1 EtOAc/heptane (25 mL:25 mL)
  4. washThe organic layer was washed with water (30 mL) and brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-098d3cbf94a24336b44601fecfddb909
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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