Boron tribromide → 2-morpholinophenol

HRID 1777145Notes

Reaction equation

HRID 1777145 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.B(Br)(Br)Br>C(Cl)Cl>[O:12]1[CH2:11][CH2:10][N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[OH:2])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 106554094-(2-methoxyphenyl)morpholine

Product 1

HCID 27953942-morpholinophenolYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(2-methoxyphenyl)morpholine (200 mg, 1.02 mmol) in CH2Cl2 (20 mL) was added BBr3 (1 mL) at 0° C. The mixture was stirred for 2 h at 0° C. The mixture was then added drop wise to ice-water (50 mL) and the mixture treated with CH2Cl2 (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the yellow solid which was used in next step without further purification (165 mg Yield 80%). LCMS (m/z): 180.1 (M+1).

Workup

  1. washThe combined organic layers were washed with brine (30 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give the yellow solid which
  5. customwas used in next step without further purification (165 mg Yield 80%)

Sources & evidence

ORD record
ord-abbf6dcb699f4c548a3b791722325087
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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