Boron tribromide → HCID 20230329, compound

HRID 527585Notes

Reaction equation

HRID 527585 reaction equation
[CH3:1][C:2]1[C:3](=[O:14])[O:4][C:5]2[C:10]([CH:11]=1)=[C:9]([O:12]C)[CH:8]=[CH:7][CH:6]=2.B(Br)(Br)Br>ClCCl>[OH:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:2]([CH3:1])[C:3](=[O:14])[O:4]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 13166821HCID 13166821, compound2×

Product 1

HCID 20230329HCID 20230329, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-5-(methyloxy)-2H-chromen-2-one (Intermediate 111, 2.5 g) in dry dichloromethane (45 ml) cooled to 0° C. was added BBr3 (39.4 ml, 39.4 mmol). The reaction mixture was warmed to room temperature and stirred at room temperature overnight under nitrogen. The reaction was then cooled to 0° C. and quenched with ice. The obtained mixture was diluted with diethyl ether and the two phases obtained were separated through a separating funnel. The aqueous phase was back-extracted with diethyl ether. The collected organic phases were dried over sodium sulphate, filtered and evaporated under vacuum to give the title compound as a light brown solid (2.225 g).

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. customquenched with ice
  3. additionThe obtained mixture was diluted with diethyl ether
  4. customthe two phases obtained
  5. customwere separated through a separating funnel
  6. extractionThe aqueous phase was back-extracted with diethyl ether
  7. dry with materialThe collected organic phases were dried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-0141635c6d1a43df9d5d2bcc71848a05
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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