Acetic Acid → HCID 117600146, compound

HRID 1497718Notes

Reaction equation

HRID 1497718 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)[CH:7]=1.[CH3:17][NH2:18].C1COCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([CH:8]([NH:18][CH3:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 6329MethylamineHCID 8028TetrahydrofuranHCID 2290095-Bromo-2-hydroxybenzophenoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 117600146HCID 117600146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-Bromo-2-hydroxy-phenyl)-phenyl-methanone (1.00 g, 3.536 mmol), 4 Å molecular sieves (1 g), and DCM are mixed then methylamine in THF (8.84 mL, 2M, 17.682 mmol) is added to followed by p-toluenesulfonic acid in acetic acid (0.474 mL, 12%, 0.354 mmol). Sodium triacetoxyborohydride (4.20 g, 19.80 mmol) is added in three separate portions. The mixture is quenched with saturated Na2CO3 solution and extracted with EtOAc. The organic phase is dried over Na2SO4 and the solvent removed on a rotary evaporator. This provides the desired compound which is used in the next step without further purification.

Workup

  1. customseparate portions
  2. customThe mixture is quenched with saturated Na2CO3 solution
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase is dried over Na2SO4
  5. customthe solvent removed on a rotary evaporator

Sources & evidence

ORD record
ord-1d5a700d584c4886bb2c28afd074fad7
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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