Sodium hydride → Tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetate

HRID 1191955Notes

Reaction equation

HRID 1191955 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.[H-].[Na+].[C:19]([O:23][C:24](=[O:27])[CH2:25]Br)([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:25][C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:27])=[CH:11][CH:10]=2)[O:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 59852411Tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetateYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (440 mg, 2.00 mmol) in anhydrous THF (40 mL) was added NaH (160 mg, 4.00 mmol). The reaction was stirred for 10 minutes at room temperature. Then, tert-butyl-bromoacetate was added and the mixture was stirred for 18 h at room temperature. Then, extracted with ethyl acetate (4×20 mL) and the organic layers were washed with an aqueous saturated solution of NaCl (3×20 mL), dried over Na2SO4, filtered and evaporated under reduced pressure. Flash chromatography of the residue on silica gel (SiO2, hexane:ethyl acetate, 9:1) afforded 96.3 mg of tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetate as a white solid (74% yield). RMN1H (CDCl3, 400 MHz): δ: 7.86-7.59; (m, 2H), 6.95-6.78; (m, 2H), 4.53; (s, 2H), 1.33; (s, 12H) ppm.

Workup

  1. stirringthe mixture was stirred for 18 h at room temperature
  2. extractionThen, extracted with ethyl acetate (4×20 mL)
  3. washthe organic layers were washed with an aqueous saturated solution of NaCl (3×20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-22bc54f9d7f848bfb0aab1439868c072
Source dataset
uspto-grants-2014_03
Patent number
US08680126B2

Reaction notes

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