Carbon tetrabromide → HCID 86751440, compound

HRID 1490131Notes

Reaction equation

HRID 1490131 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[F:25][C:26]1[CH:39]=[CH:38][C:29]([O:30][C@@H:31]2[CH2:35][CH2:34][C@H:33]([CH:36]=O)[CH2:32]2)=[CH:28][CH:27]=1>C(Cl)Cl.[Zn]>[Br:21][C:20]([Br:24])=[CH:36][C@H:33]1[CH2:34][CH2:35][C@@H:31]([O:30][C:29]2[CH:38]=[CH:39][C:26]([F:25])=[CH:27][CH:28]=2)[CH2:32]1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86751438HCID 86751438, compound

Product 1

HCID 86751440HCID 86751440, compoundYield 182.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of zinc dust (4.10 g, 63 mmol) and triphenylphosphine (16.5 g, 63 mmol) in CH2Cl2 (100 ml) was added carbon tetrabromide (20.9 g, 63 mmol). After stirring for 5 h, cis-3-(4-fluorophenoxy)cyclopentanecarbaldehyde (4.00 g, 9.2 mmol) was added to the mixture and the whole stirred overnight at room temperature (Tetrahedron Lett., 1972, 3769). The reaction mixture was filtered through a short colummn of silica gel and the filtrate concentrated in vacuo to afford 6.12 g (85%) of title compound as a light yellow oil: 1H NMR δ7.06-6.93 (m, 2H), 6.85-6.73 (m, 2H), 6.45 (d, J=9.2 Hz, 1H), 4.75-4.68 (m, 1H), 2.91-2.76 (m, 1H), 2.44-2.30 (m, 1H), 2.08-1.55 (m, 5H).

Workup

  1. stirringthe whole stirred overnight at room temperature (Tetrahedron Lett., 1972, 3769)
  2. filtrationThe reaction mixture was filtered through a short colummn of silica gel
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-2f96e1d4e8cd48cc8115713f62e7a981
Source dataset
uspto-grants-1997_10
Patent number
US05681858

Reaction notes

Loading…