Carbon tetrabromide → HCID 67111159, compound

HRID 537365Notes

Reaction equation

HRID 537365 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][C@H:5]1[CH2:9][CH2:8][C@@H:7](O)[CH2:6]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:32]>C(Cl)Cl>[Br:32][C@H:7]1[CH2:8][CH2:9][C@H:5]([CH2:4][C:3]([O:2][CH3:1])=[O:11])[CH2:6]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66935841HCID 66935841, compound

Product 1

HCID 67111159HCID 67111159, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (1S,3R)-(3-hydroxy-cyclopentyl)acetic acid methyl ester (2.0 g, 12.6 mmol) in 10 mL of DCM at 0° C. was added PPh3 (3.49 g, 13.3 mmol, 1.05 eq.), followed by CBr4 (4.41 g, 13.3 mmol, 1.05 eq.) slowly. The mixture was stirred at room temperature overnight. The reaction mixture was filtered through a thin layer silica gel and the filtrate was concentrated down. The residue was purified by silica gel chromatography with (15% EtOAc in hexanes) to provide 1.96 g of methyl 2-((1R,3S)-3-bromocyclopentyl)acetate 101.

Workup

  1. filtrationThe reaction mixture was filtered through a thin layer silica gel
  2. concentrationthe filtrate was concentrated down
  3. customThe residue was purified by silica gel chromatography with (15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-214c29b36db54666bc36bd0ad9a01cce
Source dataset
uspto-grants-2014_10
Patent number
US08859776B2

Reaction notes

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