Boron tribromide → HCID 72195104, compound

HRID 626297Notes

Reaction equation

HRID 626297 reaction equation
C([O:8][C@@H:9]([C:11]1[O:12][C:13]2[C:18]([C:19](=[O:27])[C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[C:17]([CH3:28])[CH:16]=[CH:15][CH:14]=2)[CH3:10])C1C=CC=CC=1.B(Br)(Br)Br>ClCCl>[OH:8][C@@H:9]([C:11]1[O:12][C:13]2[C:18]([C:19](=[O:27])[C:20]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[C:17]([CH3:28])[CH:16]=[CH:15][CH:14]=2)[CH3:10]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 89181747HCID 89181747, compound

Product 1

HCID 72195104HCID 72195104, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (R)-2-(1-(benzyloxy)ethyl)-5-methyl-3-phenyl-4H-chromen-4-one (0.850 g, 2.29 mmol) in dichloromethane (8.0 ml) at −78° C., boron tribromide (0.78 ml, 1M in dichloromethane, 4.58 mmol) was added slowly and maintained for 4 h. The reaction mass was quenched at −78° C. using 2N HCl (50 ml), extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was column chromatographed with ethyl acetate:petroleum ether to afford the title compound as pale-yellow liquid (0.200 g, 31%). 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.54 (t, J=8.0 Hz, 1H), 7.46-7.26 (m, 6H), 7.13 (d, J=7.4 Hz, 1H), 4.71 (q, J=6.6 Hz, 1H), 2.83 (s, 3H), 1.53 (d, J=6.6 Hz, 3H). Mass: 280.8 (M+).

Workup

  1. temperaturemaintained for 4 h
  2. customThe reaction mass was quenched at −78° C.
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customchromatographed with ethyl acetate

Sources & evidence

ORD record
ord-0bbac28a91f34031ace93da5c17e37b3
Source dataset
uspto-grants-2016_04
Patent number
US09309216B2

Reaction notes

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