Sodium borohydride → HCID 86722584, compound

HRID 1503798Notes

Reaction equation

HRID 1503798 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Br:15])[C:13]=1[Cl:14])[C:7](OC)=[O:8]>CO>[Br:3][C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=[C:12]([Br:15])[C:13]=1[Cl:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86722585HCID 86722585, compound

Product 1

HCID 86722584HCID 86722584, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (1.53 g, 40.65 mmol) was added portionwise to a stirred solution of methyl 3,5-dibromo-4-chlorobenzoate (4.45 g, 13.6 mmol) in MeOH (50 mL) at 0° C. The reaction mixture was then stirred at ambient temperature for 8 h. The volatiles were evaporated and the residue was diluted with CH2Cl2 and washed with brine followed by water. The organic layer was dried (Na2SO4), filtered and concentrated to afford the title compound as an off white solid (3.3 g, 80%): 1H NMR (300 MHz, DMSO-d6) δ 7.71 (s, 2H), 5.49 (bs, 1H), 4.48 (d, J=4.5 Hz, 2H); ESIMS m/z 297.9 ([M]+); IR (thin film) 3460, 747, 534 cm−1.

Workup

  1. customThe volatiles were evaporated
  2. additionthe residue was diluted with CH2Cl2
  3. washwashed with brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-afbe3c6699b7442f8fe58edb4db0e9f7
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

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