Phosphorus tribromide → 3-(1-Bromoethyl)-4-(thiazol-5-yl)-1H-isochromen-1-one

HRID 634393Notes

Reaction equation

HRID 634393 reaction equation
P(Br)(Br)[Br:2].O[CH:6]([C:8]1[O:9][C:10](=[O:23])[C:11]2[C:16]([C:17]=1[C:18]1[S:22][CH:21]=[N:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:7]>C(Cl)Cl.C(#N)C>[Br:2][CH:6]([C:8]1[O:9][C:10](=[O:23])[C:11]2[C:16]([C:17]=1[C:18]1[S:22][CH:21]=[N:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:7]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 1181311813-(1-Hydroxyethyl)-4-(thiazol-5-yl)-1H-isochromen-1-one

Product 1

HCID 1181310683-(1-Bromoethyl)-4-(thiazol-5-yl)-1H-isochromen-1-oneYield 45%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

1M PBr3 (0.5 ml, 0.50 mmol) in DCM was added drop-wise to of 3-(1-hydroxyethyl)-4-(thiazol-5-yl)-1H-isochromen-1-one (Intermediate B11, 102 mg, 0.372 mmol) in DCM (4 ml) and ACN (2 ml) at RT. Reaction mixture was then concentrated under reduced pressure and straightforward purified on Biotage Silica SNAP 12 g cartridge with a gradient of hexane and EtOAc to give the title compound (56 mg, 45%).

Workup

  1. customReaction mixture
  2. concentrationwas then concentrated under reduced pressure
  3. customstraightforward purified on Biotage Silica SNAP 12 g cartridge with a gradient of hexane and EtOAc

Sources & evidence

ORD record
ord-ae46feb649c7456fbc06cd3a01304248
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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