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Phosphorus tribromide → (R)-tert-Butyl(1-((2-(bromomethyl)benzyl)oxy)pent-4-en-2-yl)carbamate

HRID 1429382
Notes
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Reaction equation

HRID 1429382 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]([CH2:20][CH:21]=[CH2:22])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18]O)([CH3:4])([CH3:3])[CH3:2].P(Br)(Br)[Br:25]>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]([CH2:20][CH:21]=[CH2:22])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][Br:25])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 68233280(R)-tert-Butyl(1((2-(hydroxymethyl)benzyl)oxy)pent-4-en-2-yl)carbamate

Product 1

HCID 68233279(R)-tert-Butyl(1-((2-(bromomethyl)benzyl)oxy)pent-4-en-2-yl)carbamateYield 161.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of compound 18i (3.0 g, 9 mmol) in CCl4 (10 mL) was cooled in an ice bath. To this mixture was added PBr3 (1.0 g, 4.5 mmol) dropwise and the mixture was stirred at 0° C. for 2 hr. The mixture was quenched with water and extracted with DCM (3×50 mL). The combined organic layers were washed with brine and concentrated. The crude compound 18j (2.8 g, 80% yield) was used in the next step without purification. LCMS (m/z): 385.1 (MH+).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with DCM (3×50 mL)
  3. washThe combined organic layers were washed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-20139ca545ec4ad38c55bb56853679a8
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08940722B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes