Hydrochloric Acid → Methyl 2-(3-bromo-2-hydroxyphenyl)acetate

HRID 2173281Notes

Reaction equation

HRID 2173281 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].C(NC(C)C)(C)C.C1C(=O)N([Br:27])C(=O)C1.Cl>C(Cl)Cl>[Br:27][C:7]1[C:2]([OH:1])=[C:3]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 67184N-bromobutanimideHCID 89719Methyl (2-hydroxyphenyl)acetate

Product 1

HCID 12159074Methyl 2-(3-bromo-2-hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl (2-hydroxyphenyl)acetate (14 g, 84.3 mmol) in 100 mL of DCM was added diisopropyl-amine (1.7 g, 16.8 mmol) and NBS (15 g, 84.2 mmol) at 0° C. The mixture was stirred at 0° C. for 1 h. The reaction was poured into 1N HCl, extracted with DCM, and concentrated to give crude methyl (3-bromo-2-hydroxyphenyl)acetate. Step C: methyl (3-bromo-2-methoxyphenyl)acetate

Workup

  1. extractionextracted with DCM
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0c1962e82cb44c15944798f6bb32a5e4
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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