Carbon tetrabromide → HCID 22283544, compound

HRID 1455779Notes

Reaction equation

HRID 1455779 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]O)=[CH:10][CH:9]=1.C(Br)(Br)(Br)[Br:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:3][C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][Br:21])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 4311764Sodium borohydrideHCID 43622034HCID 43622034, compound

Product 1

HCID 22283544HCID 22283544, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Using 3,5-dichlorophenol and 4-fluorobenzaldehyde, the reaction was carried out in the same manner as in Reference Example 1 to obtain 4-(3,5-dichlorophenoxy)benzaldehyde. Subsequently, the same procedure as in Reference Example 99 was followed using sodium borohydride in place of the lithium aluminum hydride. This gave 4-(3,5-dichlorophenoxy)benzyl alcohol. The resulting alcohol (2.03 g), along with carbon tetrabromide (2.75 g), was dissolved in methylene chloride (30 mL). While this solution was stirred at 0° C., triphenyl phosphine (2.17 g) was added. The mixture was stirred at 0° C. for 1 hour and at room temperature for the subsequent 30 min. The solvent was removed under reduced pressure and the residue was purified on a silica gel column chromatography (hexane:ethyl acetate=20:1) to give the desired product as a colorless oil (3.12 g).

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 hour and at room temperature for the subsequent 30 min
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified on a silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-b9f84e861e6349b9a30b19043ef5c737
Source dataset
uspto-grants-2009_01
Patent number
US07482491B2

Reaction notes

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