Carbon tetrabromide → 1-benzhydryl-3-(2-bromoethyl)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indole

HRID 2301671Notes

Reaction equation

[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25]O)=[C:15]1[CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:66]>C(Cl)Cl>[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25][Br:66])=[C:15]1[CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution was made with 1 eq 2-[1-benzhydryl-2-({[tert -butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl]ethanol and CH2Cl2 (0.12M). Then 0.76 eq of 1,3-bis(diphenylphosphino)propane was added and the solution was cooled to 0° C. under N2. Then 1.3 eq of CBr4 was added to give a light yellow solution. The reaction was allowed to return to room temperature. After three hours and 15 minutes the solvent was removed. Purified using a flash column with silica gel and 1:5 EtOAc/Hexane as eluent to give 1-benzhydryl-3-(2-bromoethyl)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indole (yellow-brown gum) in 90% yield.

Workup

customto give a light yellow solution
customto return to room temperature
custom15 minutes the solvent was removed
customPurified

Sources & evidence

ORD record: ord-360287ea92064c09a9bcfcf0640a5596
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500853B1

Reaction notes

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