Methanol → Hydrogen Bromide

HRID 2050563Notes

Reaction equation

HRID 2050563 reaction equation
Cl.Cl.C[O:4][C:5]1[CH:6]=[C:7]2[C:10](=[CH:11][C:12]=1[O:13]C)[CH:9]([CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:8]2.B(Br)(Br)[Br:33].CO>ClCCl>[C:26]1([CH2:25][CH2:24][NH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH:9]2[CH2:8][C:7]3[C:10]2=[CH:11][C:12]([OH:13])=[C:5]([OH:4])[CH:6]=3)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1.[BrH:33]

Participants

6

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 20058565HCID 20058565, compound

Product 2

HCID 260Hydrogen BromideHCID 20058557HCID 20058557, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step (b) (3.25 g) was dissolved in dry dichloromethane (10 ml) and cooled to -78°. Boron tribromide (3.5 ml) was added, and the solution stirred at -78° for 3 hours followed by 2 hours at room temperature. Methanol (about 25 ml) was added, and the mixture reduced to dryness. The resulting white solid was crystallised from dry methanol to give the title compound as the dihydrobromide salt, 2 HBr, m.p 210°-4° (dec).

Workup

  1. temperaturecooled to -78°
  2. waitfollowed by 2 hours at room temperature
  3. customThe resulting white solid was crystallised from dry methanol

Sources & evidence

ORD record
ord-68b6e8f5a08c475096cd4a8a50611553
Source dataset
uspto-grants-1991_05
Patent number
US05013760

Reaction notes

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