Boron tribromide → 3'-Hydroxy-[1,1'-biphenyl]-3-carboxamide

HRID 1675589Notes

Reaction equation

HRID 1675589 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([NH2:17])=[O:16])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([NH2:17])=[O:16])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 671227163'-Methoxybiphenyl-3-carboxylic acid amide

Product 1

HCID 532185563'-Hydroxy-[1,1'-biphenyl]-3-carboxamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred, cooled (0° C.) solution of 3′-methoxybiphenyl-3-carboxylic acid amide (0.57 g; 2.5 mmol) in dry CH2Cl2 (28 mL), under N2 atmosphere, a 1M solution of BBr3 in CH2Cl2 (6.4 mL) was added. The mixture was stirred at room temperature for 1 h, quenched with 2N Na2CO3 and extracted with AcOEt. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. Purification of residue by column chromatography (cyclohexane/EtOAc 2:8) gave the desired product as an amorphous solid. Yield 91%. Mp: 148-51° C. (after digestion with i-Pr2O). MS (EI): m/z 213 (M+, 100%). 1H NMR (CDCl3/d6-DMSO): δ 6.06 (br s, 1H); 6.59 (m, 1H); 6.85 (m, 2H); 7.01 (t, 1H); 7.23 (t, 1H); 7.35 (br s, 1H); 7.45 (m, 1H); 7.60 (m, 1H) 7.88 (s, 1H); 8.80 (s, 1H) ppm. IR (Nujol): 3314, 3141, 1669, 1630, 1607, 1577 cm−1.

Workup

  1. customquenched with 2N Na2CO3
  2. extractionextracted with AcOEt
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification of residue by column chromatography (cyclohexane/EtOAc 2:8)

Sources & evidence

ORD record
ord-4605ec8f475247f6ba4af3531885d64c
Source dataset
uspto-grants-2011_08
Patent number
US08003693B2

Reaction notes

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