Carbon tetrabromide → HCID 86673202, compound

HRID 1746365Notes

Reaction equation

HRID 1746365 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:32])[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24]/[CH:25]=[CH:26]\[CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH3:31])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:53]>C(Cl)Cl>[Br:53][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:32])[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24]/[CH:25]=[CH:26]\[CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH3:31])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 70926492HCID 70926492, compound

Product 1

HCID 86673202HCID 86673202, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(4Z,7Z,10Z,13Z,16Z,19Z)—N-(4-(hydroxymethyl)phenyl)docosa-4,7,10,13,16,19-hexaenamide (0.5 mmol) was taken up in 5 mL of CH2Cl2 and cooled to 0° C. Triphenylphosphine (0.5 mmol) and carbon tetrabromide (0.5 mmol) were added and the resulting reaction mixture was slowly warmed to room temperature. After 2 h at room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue can be purified by silica gel chromatography to afford (4Z,7Z,10Z,13Z,16Z,19Z)—N-(4-(bromomethyl)phenyl)docosa-4,7,10,13,16,19-hexaenamide.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas slowly warmed to room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe resulting residue can be purified by silica gel chromatography

Sources & evidence

ORD record
ord-b2df7abc7df64a6ab417f8e0ff223c84
Source dataset
uspto-grants-2015_10
Patent number
US09150504B2

Reaction notes

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