Carbon tetrabromide → HCID 58822461, compound

HRID 1782086Notes

Reaction equation

HRID 1782086 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH2:20]O)[N:17]=[N:16]3)[O:11][C:10]2=[O:22])[CH:5]=[CH:6][C:7]=1[I:8].C(Br)(Br)(Br)[Br:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH2:20][Br:24])[N:17]=[N:16]3)[O:11][C:10]2=[O:22])[CH:5]=[CH:6][C:7]=1[I:8]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58822464(5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

Product 1

HCID 58822461HCID 58822461, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred mixture of (5R)-3-(3-fluoro-4-iodophenyl)-5-(4-hydroxymethyl-1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (14.7 g, 35.1 mmol) and carbon tetrabromide (12.16 g, 36.7 mmol) in dichloromethane (1 L) was treated at 0° C. with triphenylphosphine (12.34 g, 61.2 mmol). The reaction mixture was stirred for 30 minutes at 0° C. and then at room temperature overnight. The reaction mixture was applied onto a silica-gel column and eluted with hexanes:ethyl acetate (1:1) and then with ethyl acetate:methanol (95:5) to give a product that was further purified by recrystallization from ethyl acetate to give the title compound as a colorless solid (14 g).

Workup

  1. customat room temperature
  2. customovernight
  3. washeluted with hexanes:ethyl acetate (1:1)
  4. customwith ethyl acetate:methanol (95:5) to give a product that
  5. customwas further purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-cc09253487134a2a96f2d75154486a18
Source dataset
uspto-grants-2009_03
Patent number
US07498350B2

Reaction notes

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