Carbon tetrabromide → 1-(Benzyloxy)-4-(2-bromoethyl)benzene

HRID 591311Notes

Reaction equation

HRID 591311 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][CH2:14]O)=[CH:11][CH:10]=1)[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:38]>ClCCl>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][CH2:14][Br:38])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 3017260p-(Benzyloxy)phenethyl alcohol

Product 1

HCID 166388271-(Benzyloxy)-4-(2-bromoethyl)benzeneYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 3.00 g 4-benzyloxy phenethyl alcohol (13.1 mmol) in dichloromethane (132 mL) were added subsequently 5.17 g of triphenylphosphine (19.7 mmol) and 6.54 g carbon tetrabromide (19.7 mmol). The resulting mixture was stirred for 2 h at room temperature and was then evaporated. The residue was triturated with diethyl ether at −20° C. for 30 minutes, and then all solids were removed by filtration. and the filtrate was concentrated in vacuo. The residue was subjected to column chromatography on silica gel (1%→10% ethyl acetate in hexane) to give 2.80 g of the target compound (73% yield) as a pale yellow oil crystallizing upon standing.

Workup

  1. customwas then evaporated
  2. customThe residue was triturated with diethyl ether at −20° C. for 30 minutes
  3. customall solids were removed by filtration
  4. concentrationand the filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6cf237c8a11b4eff80771b83467c940b
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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