Carbon tetrabromide → 17-Acetoxy-heptadecyl bromide

HRID 1367718Notes

Reaction equation

HRID 1367718 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]O)(=[O:3])[CH3:2].C(Br)(Br)(Br)[Br:24].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][Br:24])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 8662564017-Acetoxy-heptadecanol

Product 1

HCID 5754871417-Acetoxy-heptadecyl bromideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Intermediate 17-acetoxy-heptadecanol (220 mg, 0.7 mmol) and CBr4 (302 mg, 0.91 mmol) were dissolved in CH2Cl2 (2 ml) and a solution of Ph3P (238 mg, 0.91 mmol) in CH2Cl2 (1.5 ml) was added via cannula at 0° C. The reaction was stirred at 0° C. for 2 h and then quenched with MeOH (0.3 ml), stirred for additional 10 min at room temperature, diluted with EtOAc and washed with aqueous NaHCO3 solution. The organic extract was dried over Na2SO4 and evaporated. Silica gel chromatography in hexane-EtOAc (99:1, 95:5) provided 261 mg (99%) of 17-acetoxy-heptadecyl bromide (40).

Workup

  1. customquenched with MeOH (0.3 ml)
  2. stirringstirred for additional 10 min at room temperature
  3. additiondiluted with EtOAc
  4. washwashed with aqueous NaHCO3 solution
  5. extractionThe organic extract
  6. dry with materialwas dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-c81e5ac63a5f401d8280ea09407d7b97
Source dataset
uspto-grants-2011_02
Patent number
US07893286B2

Reaction notes

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