Bromoacetyl bromide → HCID 178471769, compound

HRID 220151Notes

Reaction equation

HRID 220151 reaction equation
[C:1]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[Br:23][CH2:24][C:25](Br)=[O:26]>ClCCl>[Br:23][CH2:24][C:25]([C:4]1[CH:5]=[CH:6][C:1]([C@H:7]2[CH2:8][CH2:9][C@H:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][CH2:12]2)=[CH:2][CH:3]=1)=[O:26]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) ChlorideHCID 178471766HCID 178471766, compound

Product 1

HCID 178471769HCID 178471769, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing the product from Example 1B (1.5 g, 6.1 mmol) and AlCl3 (2.4 g, 18 mmol) in 10 mL of dichloromethane at 0° C. was added bromoacetyl bromide (0.55 mL, 6.2 mmol). The mixture was stirred at room temperature for 30 min, to one hour. Upon completion of the reaction as monitored by thin layer chromatography, the reaction mixture was poured into ice-cold water (100 mL), and extracted with dichloromethane (2×100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure, and the resulting oil was purified by flash chromatography (ethyl acetate/hexane, 1/8) to afford the title compound as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.13 (m, 2H), 1.19 (t, J=7.06 Hz, 3H), 1.50 (m, 2H), 1.70-1.85 (m, 5H), 2.22 (d, J=6.75 Hz, 2H), 2.56 (m, 1H), 4.07 (q, J=7.06 Hz, 3H), 4.88 (s, 2H), 7.41 (d J=8.28 Hz, 2H), 8.92 (d, J=8.28 Hz, 2H); MS (ESI) m/z 367.1 [M+H]+.

Workup

  1. customUpon completion of the reaction
  2. extractionextracted with dichloromethane (2×100 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe resulting oil was purified by flash chromatography (ethyl acetate/hexane, 1/8)

Sources & evidence

ORD record
ord-9f85b7878b9d4eb39ba18dd85d57ac7f
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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