Water → HCID 13108403, compound

HRID 515179Notes

Reaction equation

HRID 515179 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:7][C:6]=1[O:18]C)[CH3:2].B(Br)(Br)Br.O>ClCCl>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[CH:7][C:6]=1[OH:18])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 86699747HCID 86699747, compound

Product 1

HCID 13108403HCID 13108403, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxy-6-methyl-4-morpholin-4-yl-benzoic acid ethyl ester (7.0 g, 25.1 mmol) in dichloromethane (370 ml) is added neat boron tribromide (5.94 ml, 62.7 mmol) at −78° C. The temperature is slowly raised to room temperature over a period of 30 min and stirred for 1 h at room temperature. The reaction mixture is poured onto cold water, extracted with dichloromethane (3×30 ml). Combined organic layers are washed with brine (30 ml), dried over sodium sulfate and evaporated to dryness. The crude material is used in the next step without further purification.

Workup

  1. extractionextracted with dichloromethane (3×30 ml)
  2. washCombined organic layers are washed with brine (30 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude material is used in the next step without further purification

Sources & evidence

ORD record
ord-365070d3b6fc49788f6033a5707f0055
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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