Boron tribromide → HCID 71245529, compound

HRID 532131Notes

Reaction equation

HRID 532131 reaction equation
[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18]C)[CH:16]=2)[O:11][CH2:10][CH:9]1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[O:11][CH2:10][CH:9]1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 71245449HCID 71245449, compound

Product 1

HCID 71245529HCID 71245529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3.19 g (9.3 mmol) of ethyl 4-benzyl-6-methoxychroman-3-ylcarbamate under nitrogen atmosphere were dissolved in 90 ml of methylene dichloride. At 0° C. 28.0 ml (28.0 mmol, 1 M in methylene dichloride) of boron tribromide were added. The reaction mixture was stirred at 0° C. for 2 hours. At 0° C. saturated sodium hydrogencarbonate solution was added to the reaction mixture. The phases were separated and the aqueous phase was extracted with methylene dichloride. The combined organic layers were washed with brine, dried over MgSO4 and the solvent was evaporated to yield 3.0 g (9.2 mmol, 99) of the crude product.

Workup

  1. customAt 0° C
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with methylene dichloride
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-21773f38505c4c70915015322798d5c3
Source dataset
uspto-grants-2014_10
Patent number
US08853196B2

Reaction notes

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