Carbon tetrabromide → 2,2-Bis(6-benzyloxyhexyl)ethyl bromide

HRID 1289407Notes

Reaction equation

HRID 1289407 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:16]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:52]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:16][Br:52])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 189208622,2-Bis(6-benzyloxyhexyl)ethanol

Product 1

HCID 189208332,2-Bis(6-benzyloxyhexyl)ethyl bromideYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

First, 13.8 g of 2,2-bis(6-benzyloxyhexyl)ethanol, 10.2 g of triphenylphosphine, and 50 ml of methylene chloride were placed in a 200 ml flask. Then, 50 ml of a methylene chloride solution containing 16.1 g of carbon tetrabromide was added dropwise to the reaction mixture at room temperature, and the reaction mixture was stirred for 1 hour. The reaction mixture was washed with an aqueous solution of sodium bicarbonate and water in this order. The resultant reaction mixture was dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene) to obtain 11 g of 2,2-bis(6-benzyloxyhexyl)ethyl bromide (Y: 69%). The compound thus obtained had a purity of 97.5% by GC.

Workup

  1. additionwas added dropwise to the reaction mixture at room temperature
  2. washThe reaction mixture was washed with an aqueous solution of sodium bicarbonate and water in this order
  3. customThe resultant reaction mixture
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. distillationThereafter, the solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography (eluent: toluene)

Sources & evidence

ORD record
ord-e2cc117c2d364309b77d4aba6c91ee0c
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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