Hydrochloric Acid → HCID 23657703, compound

HRID 2220583Notes

Reaction equation

HRID 2220583 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:11][C:12]1[C:17]2[CH:18]=[C:19]([C:21]([C:23]3[O:24][C:25]4[CH:31]=[CH:30][CH:29]=[C:28]([Br:32])[C:26]=4[CH:27]=3)=O)[O:20][C:16]=2[CH:15]=[CH:14][CH:13]=1.Cl>C(OCC)C>[Br:32][C:28]1[C:26]2[CH:27]=[C:23]([CH2:21][C:19]3[O:20][C:16]4[CH:15]=[CH:14][CH:13]=[C:12]([Br:11])[C:17]=4[CH:18]=3)[O:24][C:25]=2[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 23657702HCID 23657702, compound

Product 1

HCID 23657703HCID 23657703, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of aluminum chloride (4.8 g, 11.43 mmol) in dry diethyl ether (70 mL) was added dropwise under Ar to a stirred suspension of lithium aluminum hydride (0.98 g, 25.78 mmol) in dry diethyl ether (100 mL). Pre-dried under high vacuum 82 (4.8 g, 11.43 mmol) was added in small portions. The reaction mixture was stirred at room temperature for 1 hour followed by careful addition of 2 M HCl (100 mL) and extraction with diethyl ether (2×100 mL). The ether solution was dried over CaCl2 and concentrated to provide 84 product as white crystals (3.84 g, 83%): mp 142-143° C. (diethyl ether). 1H NMR (DMSO-d6) δ7.60 (d, J=8.2 Hz, 2H), 7.47 (d, J=7.7 Hz, 2H), 7.24 (dd, J=8.2, 7.7 Hz, 2H), 6.80 (s, 2H), 4.52 (s, 2H). HPLC (method B) tR 10.67 min (100.00 area %). Anal. (C17H10Br2O3) C, H, Br.

Workup

  1. additionwas added in small portions
  2. dry with materialThe ether solution was dried over CaCl2
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ca1145a9d4974d04a8105ce75ef74b1d
Source dataset
uspto-grants-2008_08
Patent number
US07417158B2

Reaction notes

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