Boron trifluoride etherate → HCID 67508050, compound

HRID 1400019Notes

Reaction equation

HRID 1400019 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]#[N:14])[CH2:10][CH:9]2[CH2:11][OH:12])=[CH:4][CH:3]=1.B(F)(F)F.CCOCC>C1COCC1>[NH2:14][CH2:13][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:10][CH:9]1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 67508106HCID 67508106, compound

Product 1

HCID 67508050HCID 67508050, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(4-bromo-phenyl)-2-hydroxymethyl-cyclopropanecarbonitrile (12.8 g, 51.0 mmol) in anhydrous THF (150 mL) was added BF3.OEt2 (10.15 mL, 0.2 mL per mmol) and the reaction mixture was heated at 80° C. Borondimethylsulphide complex (63.4 mL, 126.9 mmol, 2M in THF) was added to the reaction mixture and heated 80° C. for 4 h. Reaction mixture was quenched by 10% hydrochloric acid at 0° C. till effervescence vanishes. The reaction mixture was washed with diethyl ether (2×70 mL) and the aqueous layer was neutralized with solid sodium bicarbonate till pH 8. The neutralized aqueous layer was extracted with ethyl acetate (3×200 mL), dried over anhydrous sodium sulphate and concentrated to yield the title compound (9.49 g, 73%) as brown oil which was used as such in the next step.

Workup

  1. temperatureheated 80° C. for 4 h
  2. customReaction mixture
  3. customwas quenched by 10% hydrochloric acid at 0° C. till effervescence
  4. washThe reaction mixture was washed with diethyl ether (2×70 mL)
  5. extractionThe neutralized aqueous layer was extracted with ethyl acetate (3×200 mL)
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dabe66c1a0e04322bb4da555575dd368
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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