Boron tribromide → HCID 86663251, compound

HRID 2070778Notes

Reaction equation

HRID 2070778 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 aded boron tribromide (40.8 mL, 1M 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 (Na2 SO4) 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. customat 0° C.
  2. additionIt was poured into ice
  3. extractionextracted with dichloromethane (×3)
  4. dry with materialthe combined organics were dried (MgSO4)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-786b813f34e84f8bbf1d9e02d96df80e
Source dataset
uspto-grants-2012_10
Patent number
US08299246B2

Reaction notes

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