Boron trifluoride etherate → 2-Hydroxy-3-linoleyloxypropylbromide

HRID 1045332Notes

Reaction equation

HRID 1045332 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[Br:2].[CH2:6]([OH:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].B(F)(F)F.CCOCC>C(Cl)Cl>[OH:5][CH:3]([CH2:4][O:24][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:1][Br:2]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 18430EpibromohydrinHCID 5365682Linoleyl alcohol

Product 1

HCID 871917832-Hydroxy-3-linoleyloxypropylbromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A 500 ml round bottom flask was charged with epibromohydrin (5.8 g, 42 mmol), linoleyl alcohol (15 g, 56 mmol), a stir bar, and then flushed with nitrogen. Anhydrous DCM (250 ml) was added via cannula, followed by BF3.Et2O (0.53 ml, 4.2 mmol), and stirred at 40° C. for 3 hours. Progress of reaction was monitored by TLC to ensure no epoxide was remaining. The reaction mixture was transferred to a 500 ml separatory funnel with DCM (2×50 ml), washed with NaHCO3 (2×200 ml), water (200 ml), brine (200 ml), dried with MgSO4, and solvent evaporated. The crude product was purified using column chromatography on silica gel (300 g) with 5-15% ether gradient in hexanes to yield 12.6 g.

Workup

  1. customflushed with nitrogen
  2. additionAnhydrous DCM (250 ml) was added via cannula
  3. customProgress of reaction
  4. washwashed with NaHCO3 (2×200 ml), water (200 ml), brine (200 ml)
  5. dry with materialdried with MgSO4, and solvent
  6. customevaporated
  7. customThe crude product was purified
  8. customto yield 12.6 g

Sources & evidence

ORD record
ord-e6ef6711c11c4787882766cab83f1fb6
Source dataset
uspto-grants-2013_10
Patent number
US08569256B2

Reaction notes

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