Methanol → HCID 131732536, compound

HRID 870385Notes

Reaction equation

HRID 870385 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:9][O:10]2)=[CH:5][CH:4]=1.B(Br)(Br)[Br:18].CO>ClCCl>[BrH:18].[CH2:14]([NH:13][CH:8]1[CH2:7][C:6]2[C:11](=[CH:12][C:3]([OH:2])=[CH:4][CH:5]=2)[O:10][CH2:9]1)[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 14103612HCID 14103612, compound

Product 1

HCID 131732536HCID 131732536, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

(7-Methoxy-chroman-3-yl)-propyl-amine (1.3 g, 5.87 mmol) was dissolved in dichloromethane (100 ml) and cooled to −78° C. Boron tribromide (11.7 ml, 122.52 mmol) was added and the reaction mixture was allowed to reach room temperature over night. The reaction mixture was cooled to −78° C. and a mixture of methanol and dichloromethane (2:3) was slowly added. The reaction mixture was allowed to reach room temperature and was then evaporated to dryness to yield the crude product (1.69 g, 5.86 mmol)

Workup

  1. waitto reach room temperature over night
  2. temperatureThe reaction mixture was cooled to −78° C.
  3. additionwas slowly added
  4. customto reach room temperature
  5. customwas then evaporated to dryness

Sources & evidence

ORD record
ord-689f8874fdba4e90a45eac29fb0d97e2
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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