Carbon tetrabromide → Br-PEG6-CH2COOtBu

HRID 1726832Notes

Reaction equation

HRID 1726832 reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]([O:29][C:30](=[O:51])[CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48]CO)([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[C:25]([O:29][C:30](=[O:51])[CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:1][Br:5])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 77078234Hydroxy-PEG6-CH2CO2tBu

Product 1

HCID 86616366Br-PEG6-CH2COOtBuYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrabromide (9.0 g, 27 mmol) and triphenyl phosphine (1.2 g, 4.5 mmol) were added to a solution of compound 2 (1.8 g, 4.5 mmol) in dry CH2Cl2 (100 mL). After stirring the reaction mixture for 5 h, the solvent was concentrated in vacuo and the residue was loaded onto a silica gel gravity column (200 g) and eluted with CH2Cl2:MeOH 100:0 to 20:1 (v/v) to afford compound 3 as a colorless oil (1.9 g, 91%).

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. washeluted with CH2Cl2:MeOH 100:0 to 20:1 (v/v)

Sources & evidence

ORD record
ord-ed728d65098c47f187eabf3bb6d70b22
Source dataset
uspto-grants-2009_02
Patent number
US07494714B2

Reaction notes

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