Benzyl Alcohol → Benzyl 4-bromobutanoate

HRID 1901426Notes

Reaction equation

HRID 1901426 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21]>O>[Br:16][CH2:17][CH2:18][CH2:19][C:20]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:21]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 702254-Bromobutyryl chloride

Product 1

HCID 3832489Benzyl 4-bromobutanoateYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzyl alcohol (28 mL, 270 mmol) and triethylamine (3.8 mL, 27 mmol) were combined and stirred over an ice bath, under nitrogen (N2). 4-Bromobutyryl chloride (1) (3.1 mL, 27 mmol) was added in a dropwise fashion, then the reaction was stirred an additional 30 minutes. The completed reaction was poured into 250 mL H2O and extracted with Et2O (3×200 mL). The ether extracts were combined, dried over MgSO4, and solvent removed in vacuo. Resulting crude product was purified by column chromatography, eluting with EtOAc/Hex (10/90) to afford 2.55 g (37%) of the desired benzyl 4-bromobutyrate (2a). 1H NMR (200 MHz, CDCl3) d 7.4 (s, 5H), 5.2 (s, 2H), 3.4 (t, 2H), 2.6 (t, 2H), 2.2 (p, 2H); mass spec (DCl, NH3) (M+NH4)+ 275.

Workup

  1. stirringthe reaction was stirred an additional 30 minutes
  2. customThe completed reaction
  3. extractionextracted with Et2O (3×200 mL)
  4. dry with materialdried over MgSO4, and solvent
  5. customremoved in vacuo
  6. customResulting crude product
  7. customwas purified by column chromatography
  8. washeluting with EtOAc/Hex (10/90)

Sources & evidence

ORD record
ord-6d571dbd44a84aa8ba333998c585eab1
Source dataset
uspto-grants-1996_11
Patent number
US05578500

Reaction notes

Loading…