Boron tribromide → HCID 86663251, compound

HRID 337102Notes

Reaction equation

HRID 337102 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:13]([NH2:15])=[O:14])[CH2:12][CH2:11][CH2:10]1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:13]([NH2:15])=[O:14])[CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66688776HCID 66688776, compound

Product 1

HCID 86663251HCID 86663251, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(2-methoxyphenyl)cyclobutanecarboxamide (Example 268a, 4.19 g) at 0° C. in dichloromethane (20 mL) was added boron tribromide (40.8 mL, 1 M in dichloromethane) and the reaction warmed to room temperature over 3 h. It was poured into ice, extracted with dichloromethane (×3) and the combined organics were dried (MgSO4) and the solvent was removed in vacuo to give crude 1-(2-hydroxyphenyl)cyclobutanecarboxamide (2.96 g). This was dissolved in DMF (20 mL) and potassium carbonate (2.14 g) and benzyl bromide (1.84 mL) were added and the reaction stirred for 16 h. Water and ethyl acetate were added and the organic layer separated. The aqueous layer was extracted further with ethyl acetate. The combined organics were washed with water (×3), brine, dried (Na2SO4) and the solvent was removed in vacuo. The residue was purified (SiO2 chromatography eluting with 5-50% ethyl acetate in iso-hexane) to afford the subtitle product (1.98 g).

Workup

  1. additionIt was poured into ice
  2. extractionextracted with dichloromethane (×3)
  3. dry with materialthe combined organics were dried (MgSO4)
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e48e5d91c12543c98d96531efbfff306
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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