Benzyl Bromide → Methyl 2-(4-benzyloxy-3-bromo-5-formyl-phenyl)acetate

HRID 712939Notes

Reaction equation

HRID 712939 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:9]=[O:10])[C:7]=1[OH:8].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)C(C)C)C>ClCCl>[CH3:15][O:14][C:12](=[O:13])[CH2:11][C:4]1[CH:5]=[C:6]([CH:9]=[O:10])[C:7]([O:8][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 57198039Methyl 2-(3-bromo-5-formyl-4-hydroxyphenyl)acetate

Product 1

HCID 58409648Methyl 2-(4-benzyloxy-3-bromo-5-formyl-phenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 250 mL round-bottomed flask with a teflon stir bar and a reflux condensor were added methyl (3-bromo-5-formyl-4-hydroxyphenyl)acetate (23.3 g, 85.3 mmol, prepared as described in Reference A above), dichloromethane (100 mL), benzyl bromide (15.32 g, 10.64 mL, 89.59 mmol), and N-ethyldiisopropylamine (11.6 g, 15.6 mL, 89.5 mmol). The reaction mixture was heated to reflux for 14 h and then allowed to cool to room temperature. Dichloromethane (100 mL) was added and the organic layer was separated and washed with 200 mL of a 3% solution of NaOH in water. The organic layer was concentrated to give (4-benzyloxy-3-bromo-5-formyl-phenyl) acetic acid methyl ester (30.65 g) as oil.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 14 h
  4. customthe organic layer was separated
  5. washwashed with 200 mL of a 3% solution of NaOH in water
  6. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-97d492a49762498daabce558716eb5b1
Source dataset
uspto-grants-2015_11
Patent number
US09181280B2

Reaction notes

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