Allyl Alcohol → HCID 22645453, compound

HRID 2414373Notes

Reaction equation

HRID 2414373 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].B(Br)(Br)Br.[CH2:18](O)[CH:19]=C>C(Cl)Cl>[Br:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH2:11][CH:18]=[CH2:19])=[O:9]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 25134Boron tribromideHCID 22645461Methyl 5-(bromomethyl)-2-fluorobenzoate

Product 1

HCID 22645453HCID 22645453, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 5-bromomethyl-2-fluorobenzoate (12.49 g, 50.6 mmol) in methylene chloride (150 mL) at 0° C. is added BBr3 (5.26 mL, 55.62 mmol) slowly, via syringe. The solution is then warmed to room temperature over 2.5 hours, and then is cooled back down to 0° C., and allyl alcohol (103 mL, 1.52 mol) is added dropwise. The solution is then stirred overnight, after which time it is diluted with CH2Cl2 (250 mL), then washed with sat'd aq. NaHCO3 (2×300 mL), brine (150 ml), and dried over MgSO4. Evaporation of solvent yields allyl 5-bromomethyl-2-fluorobenzoate.

Workup

  1. additionis added dropwise
  2. washwashed with sat'd aq. NaHCO3 (2×300 mL), brine (150 ml)
  3. dry with materialdried over MgSO4
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-9b4caee12d2040ecabda2309134f9005
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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