Hexane → (2,2-Difluoro-1,3-dioxaindan-5-yl)boronic acid

HRID 2253344Notes

Reaction equation

HRID 2253344 reaction equation
[CH:1]1[C:6](Br)=[CH:5][C:4]2[O:8][C:9]([F:12])([F:11])[O:10][C:3]=2[CH:2]=1.[Li]CCCC.CCCCCC.[B:24](OC(C)C)([O:29]C(C)C)[O:25]C(C)C>C(OCC)C>[F:11][C:9]1([F:12])[O:10][C:3]2[CH:2]=[CH:1][C:6]([B:24]([OH:29])[OH:25])=[CH:5][C:4]=2[O:8]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 21531Triisopropyl borateHCID 27362715-Bromo-2,2-difluoro-1,3-benzodioxoleHCID 178418339Butyllithium

Product 1

HCID 17750030(2,2-Difluoro-1,3-dioxaindan-5-yl)boronic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5-bromo-2,2-difluorobenzodioxole (1.18 g, 4.97 mmol) in anhydrous diethyl ether (8 mL) at −78° C. was treated with 2.5M n-BuLi in hexane (2.4 mL, 5.97 mmol), stirred for 1 hour, and treated with triisopropyl borate (1.5 mL, 6.46 mmol). The mixture was slowly warmed to room temperature and stirred for about 18 hours. The reaction was quenched with saturated NH4Cl/10% HCl and extracted with ethyl acetate. The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was used directly without further purification. 1H NMR (CD3OD) δ 7.26-7.11 (m, 3H).

Workup

  1. stirringstirred for about 18 hours
  2. customThe reaction was quenched with saturated NH4Cl/10% HCl
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was used directly without further purification

Sources & evidence

ORD record
ord-f4e7d11f00dc4b8187e44bfd1c689ba6
Source dataset
uspto-grants-2008_01
Patent number
US07323570B2

Reaction notes

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