Carbon tetrabromide → HCID 22283544, compound

HRID 1062910Notes

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

Conditions

Temperature: 0 °C

Procedure

Using 3,5-dichlorophenol and 4-fluorobenzaldehyde, reactions were carried out in the same manner as in Reference Example 1 to obtain 4-(3,5-dichlorophenoxy)benzaldehyde. The subsequent reactions were carried out in the same manner as in Reference Example 123, except that sodium borohydride was used in place of lithium aluminum hydride. This gave 4-(3,5-dichlorophenoxy)benzyl alcohol. The alcohol (2.03 g) and carbon tetrabromide (2.75 g) in methylene chloride (30 mL) were stirred at 0° C., and triphenyl phosphine (2.17 g) was added to the solution. The resulting mixture was stirred for 1 hour at 0° C. and then for 30 minutes at room temperature. Subsequently, the solvent was removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1). In this manner, the desired product (3.12 g) was obtained as a colorless oil.

Workup

waitfor 30 minutes at room temperature
customSubsequently, the solvent was removed by distillation under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record: ord-c942927ac4814d749021a07922483032
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06963012B2

Reaction notes

Loading…