Carbon tetrabromide → 16-Bromo-1-phenyl-2,5,8,11,14-pentaoxahexadecane

HRID 2075630Notes

Reaction equation

HRID 2075630 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:25][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 135536921-Phenyl-2,5,8,11,14-pentaoxahexadecan-16-ol

Product 1

HCID 5868775516-Bromo-1-phenyl-2,5,8,11,14-pentaoxahexadecaneYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Compound 19 (2.04 g, 6.21 mmol) in methylene chloride (20 ml), a solution of carbon tetrabromide (4.12 g, 12.4 mmol) in methylene chloride (10 ml) was added at room temperature; after cooling with ice, triphenylphosphine (2.51 g, 12.4 mmol) was added. The water bath was removed, and this was followed by stirring at room temperature for 1 hour. After concentration under reduced pressure, the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1-1:1)) to yield Compound 20 (light-yellow oil 2.14 g, 88%).

Workup

  1. additionwas added
  2. customThe water bath was removed
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue obtained
  5. customwas purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1-1:1))

Sources & evidence

ORD record
ord-5c9f9082ff7f4548bc8647d1aae6b397
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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