Bromoacetyl bromide → Pyren-1-ylmethyl 2-bromoacetate

HRID 571574Notes

Reaction equation

HRID 571574 reaction equation
[C:1]1([CH2:17][OH:18])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[Br:19][CH2:20][C:21](Br)=[O:22]>CN(C=O)C.ClCCl>[Br:19][CH2:20][C:21]([O:18][CH2:17][C:1]1[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1)=[O:22]

Participants

5

Reactant 2

HCID 61147Bromoacetyl bromideHCID 1049771-Pyrenemethanol

Product 1

HCID 15686801Pyren-1-ylmethyl 2-bromoacetateYield 100.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Pyrenemethanol (Pyr-OH) (109.6 mg, 0.47 mmol) in 1.0 mL DMF (anh) was treated with 180 μL TEA (anh, 1.29 mmol) and 2-bromoacetyl bromide (132.2 μL, 1.50 mmol) in 1 mL dichloromethane. The mixture was stirred at RT (˜23° C.) for 17 hours. After the solvent was evaporated, the crude product was purified by silica gel column (Hex/EtOAc=2/1) to give 167 mg final product as a yellow solid (yield 90%). 1H NMR (CDCl3, 500 MHz): δ 8.28-8.03 (m, 9H, ArH), 5.94 (s, 2H, ArCH2), 3.90 (s, 2H, CH2Br). ESI: 375, [M+Na]+.

Workup

  1. customAfter the solvent was evaporated
  2. customthe crude product was purified by silica gel column (Hex/EtOAc=2/1)

Sources & evidence

ORD record
ord-1f6638ac4c364df394bacf3e07c31fe7
Source dataset
uspto-grants-2015_05
Patent number
US09028880B2

Reaction notes

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