Carbon tetrabromide → HCID 54080281, compound

HRID 363012Notes

Reaction equation

HRID 363012 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13]O)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:43]>C1COCC1>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][Br:43])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine2×HCID 53721633HCID 53721633, compound

Product 1

HCID 54080281HCID 54080281, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-4 (3.6 g, 12 mmol), triphenyl phosphine (3.1 g, 11.8 mmol) in THF (100 ml) was treated with carbon tetrabromide (3.9 g, 11.8 mmol). After 12 h additional triphenylphosphine (3.1 g, 11.8 mmol) was added and the mixture allowed to stir at room temperature overnight. Some triphenyl phosphine oxide was then filtered off and the filtrate concentrated to dryness. The residue was chromatographed on a Still column (70 mm) and the product eluted with 5% EtOAc-hexane to yield 1-5.

Workup

  1. filtrationSome triphenyl phosphine oxide was then filtered off
  2. concentrationthe filtrate concentrated to dryness
  3. customThe residue was chromatographed on a Still column (70 mm)
  4. washthe product eluted with 5% EtOAc-hexane
  5. customto yield 1-5

Sources & evidence

ORD record
ord-2a44a0c04d3a4e999e68cdc41521cddc
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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