Methanol → HCID 20230697, compound

HRID 2290911Notes

Reaction equation

HRID 2290911 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[CH2:21][CH:20]3[CH:15]([CH2:16][CH2:17][C:18]4[C:25]([O:26]C)=[C:24]([O:28]C)[CH:23]=[CH:22][C:19]=43)[CH2:14]2)=[CH:6][CH:5]=1.B(Br)(Br)[Br:31].CO>C(Cl)Cl>[BrH:31].[BrH:31].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[CH2:21][CH:20]3[CH:15]([CH2:16][CH2:17][C:18]4[C:25]([OH:26])=[C:24]([OH:28])[CH:23]=[CH:22][C:19]=43)[CH2:14]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 20230749HCID 20230749, compound

Product 1

HCID 20230697HCID 20230697, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of the compound of example 16 (0.41 g, 0.92 mmole) in CH2Cl2 (9.2 mL) was stirred under N2 at -78° C. as a solution of BBr3 (0.37 mL, 3.9 mmole) in 2.1 mL of CH2Cl2 was added dropwise. The reaction mixture was stirred for 1 hour at -78° C., 21/4 hr at 0°, and 21/4 hr at room temperature, then was cooled again to -78° as MeOH (7.3 mL) was added slowly. The reaction mixture was allowed to warm to room temperature overnight. The precipitate was filtered, washed with Et2O, and dried (in-vacuo) to yield 0.30 g light yellow powder; mp 290°; M+ 338.

Workup

  1. additionwas added dropwise
  2. additionwas added slowly
  3. temperatureto warm to room temperature overnight
  4. filtrationThe precipitate was filtered
  5. washwashed with Et2O
  6. customdried (in-vacuo)
  7. customto yield 0.30 g light yellow powder

Sources & evidence

ORD record
ord-62aeaa2802af471386914505766a11a9
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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