Carbon tetrabromide → HCID 135516505, compound

HRID 1591787Notes

Reaction equation

HRID 1591787 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[O:12][CH:13]=[C:14]([CH2:16]O)[N:15]=2)[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[OH:22])([CH3:4])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:24].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>ClCCl>[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[O:12][CH:13]=[C:14]([CH2:16][Br:24])[N:15]=2)[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[OH:22])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 135418213HCID 135418213, compound

Product 1

HCID 135516505HCID 135516505, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The compound of Example 351 (4.70 mmol) is dissolved in dichloromethane (30 ml). After adding CBr4 (2.02 g; 6.10 mmol), the reaction medium is cooled down to 0° C. PPh3 (1.48 g; 5.63 mmol) is added by fractions then the mixture is left to return to ambient temperature. The reaction medium is then poured into ice-cold water before being extracted with dichloromethane. The organic phase is washed with salt water before being dried over magnesium sulphate, filtered and concentrated under vacuum. The crude oil obtained is sufficiently pure to be used directly in the following stage.

Workup

  1. waitthe mixture is left
  2. customto return to ambient temperature
  3. additionThe reaction medium is then poured into ice-cold water
  4. extractionbefore being extracted with dichloromethane
  5. washThe organic phase is washed with salt water
  6. dry with materialbefore being dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude oil obtained

Sources & evidence

ORD record
ord-77177522b3b94dd7b79d9db27c56377d
Source dataset
uspto-grants-2007_11
Patent number
US07291641B2

Reaction notes

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