Water → HCID 16041824, compound

HRID 1887470Notes

Reaction equation

HRID 1887470 reaction equation
[OH:1][C:2]1[C:3]([O:24]C)=[CH:4][C:5]2[CH2:14][CH2:13][N:12]3[CH:7]([CH2:8][C:9]4[C:18]([Cl:19])=[CH:17][C:16]([O:20]C)=[C:15]([OH:22])[C:10]=4[CH2:11]3)[C:6]=2[CH:23]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:1][C:2]1[C:3]([OH:24])=[CH:4][C:5]2[CH2:14][CH2:13][N:12]3[CH:7]([CH2:8][C:9]4[C:18]([Cl:19])=[CH:17][C:16]([OH:20])=[C:15]([OH:22])[C:10]=4[CH2:11]3)[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 10451265HCID 10451265, compound

Product 1

HCID 16041824HCID 16041824, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A product obtained in Example 1 (0.3 g, 0.66 mmol) was dissolved in CH2Cl2 (20 ml), adding a solution of BBr3 (0.32 ml) in CH2Cl2 (5 ml) under ice-salt bath. The mixture was stirred for 1 hours at this temperature, then stirred at room temperature overnight. The reactant solution produced yellow precipitate. The mixture was poured into water and stirred for 30 minute. After filtering, the solid was dissolved with methanol. Then the mixture was filtered. The filtrate was evaporated under reduced pressure, followed by recrystallizing with methanol to give yellow solid (0.15 g, 67.7%). mp 295˜296° C. 1HNMR (DMSO-d6) δ: 2.65˜2.86 (3H, m, CH2), 3.05˜3.63 (5H, m, CH2 or N—CH), 4.29 (1H, d, CH2), 6.59 (1H, s, ArH), 6.81 (1H, s, ArH), 6.92 (1H, s, ArH). MS (EI) m/z: 333 (M+), 299, 164 (base), 107, 80.

Workup

  1. stirringstirred at room temperature overnight
  2. customThe reactant solution produced yellow precipitate
  3. stirringstirred for 30 minute
  4. filtrationAfter filtering
  5. dissolutionthe solid was dissolved with methanol
  6. filtrationThen the mixture was filtered
  7. customThe filtrate was evaporated under reduced pressure
  8. customby recrystallizing with methanol

Sources & evidence

ORD record
ord-99458e0b7acd40f7974022f2568bad2b
Source dataset
uspto-grants-2013_08
Patent number
US08501762B2

Reaction notes

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