Boron tribromide → HCID 86694456, compound

HRID 1519539Notes

Reaction equation

HRID 1519539 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]#[N:13])[O:8][CH2:7][CH2:6]/[C:5]/2=[CH:14]\[O:15]C.BrB(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]#[N:13])[O:8][CH2:7][CH2:6][CH:5]2[CH:14]=[O:15]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 86694455HCID 86694455, compound

Product 1

HCID 86694456HCID 86694456, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

(4E)-6-fluoro-4-(methyoxymethylidene)-3,4-dihydro-2H-chromene-7-carbonitrile (38 mg, 0.17 mmol) was dissolved in dichloromethane (6 mL). The solution was cooled to −78° C. To above solution was added tribromoborane (260 μL, 1 M, 0.26 mmol) dropwise. The reaction was stirred for 30 min at −78° C. To the reaction mixture was added saturated sodium bicarbonate, extracted with dichloromethane (2×20 mL). The organic phase was washed with brine (5 mL), dried over anhydrous Na2SO4, filtered, concentrated and used without purification.

Workup

  1. extractionextracted with dichloromethane (2×20 mL)
  2. washThe organic phase was washed with brine (5 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customused without purification

Sources & evidence

ORD record
ord-804aae561eea4e858d4222061ea9215c
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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