HCID 20213340, compound → HCID 57015737, compound

HRID 922311Notes

Reaction equation

HRID 922311 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 20213340HCID 20213340, compound

Product 1

HCID 57015737HCID 57015737, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-(4′-methoxybiphenyl-4-yl)propanoate (0.35 g, 1.2 mmol) in dichloromethane was added borontribromide (0.4 g, 1.6 mmol) at 0° C. and stirred at RT for 30 min, Reaction quenched with ethanol and diluted with water and extracted with dichloromethane, organic layer was washed with NaHCO3, water and brine solution and dried over sodium sulphate then concentrated to white solid (0.27 g, Yield: 83.3%): 1H NMR (300 MHz, CDCl3): δ 9.49 (s, 1H), 7.43-7.48 (t, 4H), 7.23-7.26 (d, 2H), 6.81-6.84 (d, 2H), 4.01-4.08 (m, 2H), 2.83-2.88 (t, 2H), 2.59-2.64 (t, 2H), 1.13-1.18 (t, 3H).

Workup

  1. customReaction
  2. customquenched with ethanol
  3. additiondiluted with water
  4. extractionextracted with dichloromethane, organic layer
  5. washwas washed with NaHCO3, water and brine solution
  6. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-1a695c7553fa44d0bf95e03eed99cae1
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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